WO2007105622A1 - Méthode de production d'un composé hétérocyclique - Google Patents

Méthode de production d'un composé hétérocyclique Download PDF

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WO2007105622A1
WO2007105622A1 PCT/JP2007/054644 JP2007054644W WO2007105622A1 WO 2007105622 A1 WO2007105622 A1 WO 2007105622A1 JP 2007054644 W JP2007054644 W JP 2007054644W WO 2007105622 A1 WO2007105622 A1 WO 2007105622A1
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group
substituent
formula
aryl
heterocyclic
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PCT/JP2007/054644
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English (en)
Japanese (ja)
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Kazuhiko Takai
Yoichiro Kuninobu
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National University Corporation Okayama University
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Priority to JP2008505106A priority Critical patent/JP5181190B2/ja
Publication of WO2007105622A1 publication Critical patent/WO2007105622A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Definitions

  • the present invention relates to a method for producing a heterocyclic compound, in particular, isobenzofuran or a similar heterocyclic compound.
  • Heterocyclic compounds having a ⁇ -conjugated system are also attracting interest as materials for organic electroluminescence (EL) devices, organic field effect transistor (FET) devices, fluorescent dyes, and the like.
  • EL organic electroluminescence
  • FET organic field effect transistor
  • One such heterocyclic compound is isobenzofuran or a similar compound. So far, several methods have been reported for synthesizing isobenzofuran and its compounds in which oxygen atoms are replaced by sulfur atoms or selenium atoms.
  • Non-Patent Document 1 describes a method of synthesizing 1,3-diphenylisobenzofuran by reducing orthodibenzoylbenzene with potassium borohydride and then dehydrating it using an acid catalyst. Is described. Then, 1,3-diphenylisobenzofuran obtained by this method is reacted with pentasulfurium diphosphorusen to produce 1,3-diphenylbenzo [c] thiophene (isothianaphthene). Is also obtained.
  • Non-Patent Document 2 describes a method of synthesizing 1,3-diphenylisobenzofuran by oxidizing 2,2-dimethyl-1,3-diphenylisoindene in air.
  • Non-Patent Document 3 describes a method of synthesizing 1,3-diphenylisobenzofuran by reacting benzoyl chloride to a dilithium salt of benzophenosylhydrazone and then reacting with lithium bromide. Yes.
  • benzo [c] selenophene is obtained by reacting isobenzofuran with Woollins reagent ([PhP (Se) ( ⁇ -Se)]).
  • the conventional synthesis methods often require special raw materials as shown in these examples. Therefore, the synthesis of the raw materials required multiple steps, which required a long time and high manufacturing costs. In addition, it was not easy to introduce a substituent at an arbitrary position of the ring skeleton of the obtained heterocyclic compound. In addition, the reactant In many cases, there were problems such as safety, the need for a large amount of solvent, and the formation of a large amount of by-products.
  • Non-Patent Document 5 a method of synthesizing an indene derivative by reacting with an acetylene after activating a CH bond at the ortho-position of an aromatic ring to which an imino group is bonded with a rhodium compound, Similarly, a method for synthesizing a phthalimidine derivative by reacting with an isocyanate after being activated has already been reported by the inventors of the present application.
  • Non-Patent Document 1 M. P. Cava, 2 others, Journal of Organic Chemistry, 1960, Vol. 25, p. 1481-1484
  • Non-Patent Document 2 E. Johansson, 1 other, Journal of Organic Chemistry, 1981, Vol. 46, p. 3752-3754
  • Non-Patent Document 3 J. T. Sharp, 1 other, Tetrahedron Letters, 1986, Vol. 27, p. 869 -872
  • Non-Patent Document 4 A. K. Mohanakrishnan, 1 other, Tetrahedron Letters, 2005, 46, p. 7201-7204
  • Non-Patent Document 5 Y. Kuninobu, 3 others, Journal of the American Chemical Society, 2006, No. 128, p. 202-209
  • the present invention has been made to solve the above-described problems, and provides a method for synthesizing isobenzofuran and similar heterocyclic compounds in a short reaction step that is easily available. It is the purpose.
  • the above object is to provide an aromatic imine having at least one aromatic ring bonded to a carbon atom of an imino group and having at least one hydrogen atom at the position of imino group ortho in the aromatic ring, an aldehyde, A group consisting of thioaldehyde, selenaldehyde, and terucaldehyde also selected from the group consisting of isobenzofuran, isothianaphthene, isoselenanaphthene and isotellananaphthene, characterized by reacting with one compound It is solved by providing a process for the preparation of one kind of heterocyclic compound in which force is also selected. Specifically, the above problem is solved by the following formula (I)
  • R ⁇ R 2 , R 3 and R 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a substituent.
  • R 5 and R 6 are each independently , A hydrogen atom, an alkyl group which may have a substituent, an alkyl group which may have a substituent,
  • An aryl group which may have a substituent an aryl group which may have a substituent, an aryl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It may have a cycloalkyl group or a substituent, R ⁇ R 2 , R 3 , R 4 , R 5 and R 6 may be bonded to each other to form a ring. And a compound of the following formula (II)
  • R 7 has an aryl group that may have a substituent, an aromatic heterocyclic group that may have a substituent, an aryl group that may have a substituent, or a substituent.
  • X is an oxygen atom, a sulfur atom, a selenium atom and It is one selected from the group of tellurium nuclear power.
  • R 5 may have a substituent, may have a aryl group, or may have a substituent !, an aromatic heterocyclic group, an optionally substituted aryl group or substituent.
  • X is an oxygen atom.
  • Such catalysts that are preferably reacted in the presence of a catalyst comprising a transition metal compound include transition metal compounds belonging to Group 7, Group 8, Group 9 or Group 10 of the Periodic Table, among them.
  • rhenium compounds, particularly rhenium (I) compounds are preferably used.
  • the reaction it is represented by the formula (I). It is preferable that the molar ratio ( ⁇ ) of the compound represented by the formula (II) to the compound to be reacted is 1.5 or more.
  • X is an oxygen atom, it is preferable to proceed the reaction while removing generated water from the reaction system.
  • the present invention relates to an aromatic imine having at least one aromatic ring bonded to a carbon atom of an imino group and having at least one hydrogen atom at the position of the imino group ortho in the aromatic ring, and an aldehyde , Thioaldehyde, selenoaldehyde, and terucaldehyde are also selected.
  • This is a method for producing one kind of selected heterocyclic compound.
  • the aromatic imine may have an arbitrary substituent that does not inhibit the progress of the reaction of the present invention.
  • a compound represented by the following formula (I) is preferably used.
  • R 2, R 3 and R 4 are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, which may have a substituent Alkyl group, aryl group which may have a substituent, aryl alkyl group which may have a substituent, aryl hydrocarbon group which may have a substituent, aryl which may have a substituent
  • Good carboxyl group or salt thereof alkyl carbo group, aryl carbo group, alkyloxy carbo group, aryloxy carbo ol group, alkyl group, carboxy group, ally carboxy group, protective group Amino group, alkylamino group, arylamino group, am
  • the monovalent substituents RR 2 , R 3 and R 4 bonded to the aromatic ring in the formula (I) are not particularly limited as long as they do not inhibit the progress of the reaction of the present invention. Instead, the above-mentioned various substituents can be employed. However, as shown in the formula (I), it is necessary that at least one hydrogen atom is bonded to the ortho position as viewed from the imino group in the aromatic ring. This is because it is presumed that the reaction proceeds by activating the CH bond at the ortho position as viewed from the force imino group that explains the estimation mechanism of the reaction of the present invention.
  • the substituents R 1 R 2 , R 3 and R 4 may have a substituent !, an alkyl group, an optionally substituted alkenyl group, and a substituent. It may have an alkyl group or a substituent.
  • the number of carbon atoms of the thiol group, arylsulfol group, alkylazo group and allylazo group is not particularly limited, and may be a polymer chain. However, it is usually 1 to 20, and preferably 1 to 10.
  • R 5 may have a hydrogen atom, a substituent, an alkyl group, a substituent, an alkyl group, or a substituent.
  • R 5 is preferably not a hydrogen atom.
  • R 5 has an aryl group which may have a substituent, an aromatic heterocyclic group or a substituent which may have a substituent.
  • each substituent of R 5 is not particularly limited, and may be a polymer chain, but is usually 1 to 20, preferably 6 to 20, more preferably 6 to 10. It is. Preferable specific examples thereof include a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a substituent which may have a substituent, and a cinnamyl group.
  • R 6 may have a hydrogen atom, a substituent, an alkyl group, or a substituent.
  • Alkyl group, alkyl group which may have a substituent, aryl group which may have a substituent, aryl alkyl group which may have a substituent, and substituent An arylalkyl group that may be substituted, an arylalkyl group that may have a substituent, a cycloalkyl group that may have a substituent, or a heterocyclic group that may have a substituent.
  • R 6 is not a hydrogen atom.
  • each substituent of R 6 is not particularly limited and may be a polymer chain, but is usually 1 to 20, preferably 6 to 20, more preferably 6 to: LO.
  • R 6 is a substituent that is not finally incorporated into the target product but is incorporated into the by-product amine or aldimine.
  • Preferable specific examples include a phenyl group and a benzyl group.
  • R 2 , R 3 , R 4 , R 5 and R 6 may be bonded to each other to form a ring.
  • R 3 and R 4 adjacent substituents may be bonded to form a ring, or distant substituents may be bonded to form a ring.
  • R 5 is It may be bonded to R 2 , R 3 or R 4 .
  • R 6 is In this case, it may be bonded to R 3 , R 4, or R 5, and in this case, there is an amine produced as a by-product of the reaction, and aldimine is incorporated into the heterocyclic compound shown by the formula (III). Become.
  • Three or more substituents of R 2 , R 3 , R 4 , R 5 and R 6 may be bonded to each other.
  • the ring thus formed may be an aromatic ring or a non-aromatic ring.
  • the number of carbon atoms of the substituent in the case of forming a ring is not particularly limited, and the ring may be bonded to the polymer chain, but is usually 1 to 20, preferably 6 to 20, Preferably it is 6-10.
  • the carbon number here is the total number of carbon atoms of the substituents that are bonded to each other to form a ring. For example, when a naphthalene ring is formed by condensing a benzene ring at the R 1 and R 2 positions, the carbon number is counted as 4.
  • the compound may have an arbitrary substituent that does not inhibit the progress of the reaction of the present invention. Specifically, a compound represented by the following formula ( ⁇ ) is preferably used.
  • R 7 has an aryl group that may have a substituent, an aromatic heterocyclic group that may have a substituent, an aryl group that may have a substituent, or a substituent.
  • X is an oxygen atom, a sulfur atom, a selenium atom and It is one selected from the group of tellurium nuclear power.
  • R 7 is, I may have a substituent!, Have Ariru group, the substituents! ⁇ ⁇ Aromatic heterocyclic group, optionally substituted aryl alkenyl group, optionally substituted aryl hydrocarbon group, optionally substituted, alkenyl group or substituent
  • An alkynyl group which may have That is, it has an aromatic ring or an unsaturated bond that can be conjugated with a C X bond.
  • R 7 may have an aryl group or a substituent which may have a substituent.
  • R 7 may preferably have an aromatic heterocyclic group, a substituent, an arylalkyl group or a substituent, and may be an arylalkyl group.
  • R 7 include a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a cinnamyl group which may have a substituent.
  • a good yield can be obtained regardless of whether R 7 is a phenyl group having an electron-withdrawing group or a phenyl group having an electron-donating group. As a result, it is possible to introduce various substituents.
  • X is an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atomic force, which is one kind selected.
  • the compound represented by the formula (II) is an aldehyde.
  • the compound represented by the formula (II) is thioaldehyde.
  • X is a selenium atom
  • the compound represented by the formula (II) is selenoaldehyde.
  • X is a tellurium atom
  • the compound represented by the formula ( ⁇ ) is a tellurium aldehyde.
  • These compounds may form stable trimers. For example, in the case of thioaldehyde, a trithian ring is formed to form a trimer. In the production method of the present invention, this In this case, the reaction proceeds via the monomer produced in the reaction system.
  • X is one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and tellurium atomic energy.
  • the heterocyclic compound represented by the formula ( ⁇ ) is isobenzofuran (2-benzofuran: benzo [c] furan).
  • the heterocyclic compound represented by the formula ( ⁇ ) is isothianaphthene (2-benzothiophene (benzo [c] thiophene).
  • the formula (III) is isoselenanaphthene (2-benzoselenophene: benzo [c] selenophene)
  • the heterocyclic compound represented by formula (III) is Isotellanaphthene (2-benzoterphene: benzo [c] terphene).
  • the substituents of RR 2 , R 3 , R 4 , R 5 and R 7 are each a compound represented by the formula (I) as a raw material And from a compound represented by the formula ( ⁇ ).
  • Both the compound represented by the formula (I) and the compound represented by the formula ( ⁇ ⁇ ⁇ ) are compounds that can be easily introduced with various substituents, and as a result, have various substituents at desired positions.
  • the heterocyclic compound represented by the formula ( ⁇ ) can be easily produced in one step.
  • the reaction described above is represented by a reaction formula by taking the case where X is an oxygen atom as an example.
  • 1 mol of the compound represented by the formula (IV) (aldimine) and 1 mol of water are by-produced.
  • Half of the compound represented by the formula (Ila) reacts directly with the compound represented by the formula (I), and the other half captures the by-produced amine during the reaction to obtain the compound represented by the formula (IV) Is consumed to form).
  • R 6 and R 7 in the compound represented by the formula (IV) have the same meanings as the formula (I) and the formula (II).
  • the reaction is preferably performed with the molar ratio ( ⁇ ) of the compound represented by the formula (II) to the compound represented by the formula (I) being 1.5 or more. It is more preferable.
  • the molar ratio ( ⁇ ) is usually 10 or less, preferably 5 or less.
  • the method of mixing and reacting the compound represented by the formula (I) and the compound represented by the formula ( ⁇ ) is not particularly limited. You may make it react in a solution using a solvent, and you may make it react without a solvent.
  • the solvent that can be used is not particularly limited, but an aprotic organic solvent such as hexane, benzene, toluene, dichloroethane, and tetrahydrofuran is preferable. Of these, hydrocarbon solvents or halogen-containing hydrocarbon solvents are preferably used.
  • X in the formula (II) is an oxygen atom, water is by-produced as the reaction proceeds. Therefore, it is preferable to proceed the reaction while removing the produced water from the reaction system.
  • the method for removing water from the reaction system is not particularly limited.
  • a water-absorbing agent such as molecular sieves may coexist in the reaction system, and water is removed when the solvent is heated to reflux. You may leave.
  • the reaction temperature is not particularly limited, but a temperature of 0 to 300 ° C is usually employed. Preferably, it is 50 ° C or higher and 200 ° C or lower.
  • the compound represented by the formula (I) and the compound represented by the formula ( ⁇ ) are reacted, it is preferably reacted in the presence of a catalyst composed of a transition metal compound.
  • the amount of the transition metal compound used is not particularly limited, but the transition metal compound is used in an amount of 0.001 to 0.5 times the number of moles of the compound represented by the formula (I) on a metal atom basis. Is preferred. From the viewpoint of the reaction rate and yield, the amount of the transition metal compound used is more preferably 0.005 times or more, more preferably 0. 0,5 times the number of moles of the compound represented by formula (I). 01 times or more. On the other hand, from the viewpoint of reducing manufacturing costs and waste, the amount of transition metal compound used is more preferably 0.2 times or less the number of moles of the compound represented by formula (I). Is less than 0.1 times.
  • the transition metal compound used as the catalyst is preferably a transition metal compound belonging to Group 7, Group 8, Group 9 or Group 10 of the periodic table. This is because these transition metal compounds are generally considered to have the ability to activate C—H bonds.
  • compounds of rhenium, ruthenium, rhodium, iridium and palladium are suitable. Of these, rhenium compounds, particularly monovalent rhenium compounds (rhenium (I) compounds) are preferably used.
  • the rhenium compound is not particularly limited, but is preferably a compound containing a ligand (complex).
  • the ligand includes halogen atoms such as bromine and chlorine, carbon monoxide, tetrahydrofuran (thf ) And the like.
  • halogen atoms such as bromine and chlorine
  • carbon monoxide tetrahydrofuran (thf )
  • rhenium compound include [ReBr (CO) (thf)], ReBr (CO), and ReCl (CO).
  • the valence of the rhenium compound to be added may be different as long as the rhenium (I) compound is present in the reaction system.
  • a zero-valent rhenium compound may be oxidized in the reaction system, and a polyvalent rhenium compound may be reduced in the reaction system.
  • reaction mechanism of the present invention is not necessarily clear, when a rhenium catalyst is used and an aldehyde is used as the compound represented by the formula (II), a mechanism such as the following formula (2) is used. Is estimated. First, the CH bond at the ortho position of the aromatic ring is activated by a rhenium catalyst, and an aldehyde is inserted into the formed C—Re bond. Next, find it in the molecule. A cyclization reaction proceeds nuclearly, rhenium salt is reductively eliminated, and amine is eliminated. The released amine reacts with the aldehyde and dehydrates to form aldimine.
  • the heterocyclic compound represented by the formula (III) thus obtained has a long and ⁇ -conjugated system, it is an organic electroluminescence (EL) device, an organic field effect transistor (FET) device, an organic compound. It is promising as a material for light emitting diodes and fluorescent dyes. According to the production method of the present invention, a heterocyclic compound having various substituents at desired positions can be easily produced in one step. Therefore, it becomes easy to adjust the physical properties of the heterocyclic compound represented by the formula (III), and the target compound based on the molecular design can be easily obtained.
  • EL organic electroluminescence
  • FET organic field effect transistor
  • the compound (B1553) represented by the following formulas (3) and (4) has an electron transport capability and a hole transfer capacity of 1 ⁇ 1 ⁇
  • HT layer hole transport layer
  • B1553 can be easily manufactured by the method shown in the equation (4).
  • the heterocyclic compound represented by the formula (III) is also useful as a reaction intermediate.
  • the heterocyclic compound represented by the formula (III) is reacted with olefin (V) or acetylene (VII) to advance the Diels-Alder reaction.
  • the diels-alder reaction may proceed by reacting olefin (V) or acetylene (VII) with a bicyclic compound synthesized in advance.
  • the reaction is allowed to proceed in the presence of a compound represented by the formula (I), a compound represented by the formula ( ⁇ ), olefin (V) or acetylene (VII), and represented by the formula (III) produced.
  • the heterocyclic compound is preferably captured by olefin (V) or acetylene (VII) in the reaction system. This is a particularly effective technique when the heterocyclic compound represented by the formula (III) is unstable. In this case, it is preferable that olefin (V) or acetylene (VII) is blended in an excessive amount with respect to the compound represented by formula (I).
  • the Diels-Alder attached product represented by the following formula (VI) is obtained. can get.
  • the compound obtained by the Diels-Alder reaction as described above has a skeleton in which a large number of rings are bonded, and often has a long ⁇ -conjugated system. Therefore, an organic electroluminescence (EL) device or It is promising as a material for organic field-effect transistor (FET) elements, organic light-emitting diodes, and fluorescent dyes.
  • EL organic electroluminescence
  • FET organic field-effect transistor
  • a polycyclic compound having various substituents at desired positions can be easily produced.
  • a new blue light-emitting substance, 7, 16-dihydroheptacene derivative has been reported to be synthesized by the method of the following formula (5). (J. Org. Chem. 2006, 71, 4085), but requires a multi-step reaction.
  • the manufacturing method of the present invention as shown in the equation (6), the number of steps can be greatly reduced.
  • Example 1 The compound represented by formula (I) is an aromatic imine, N- (diphenylmethylene) benzenamine 129 mg (0.500 mmol), and the compound represented by formula (II) is benzaldehyde 1 02 (1. OOmmol). ), [ReBr (CO) (thf)] 10.6 mg (0.O125 mmol) as a catalyst,
  • Examples 2-7 A heterocycle represented by the formula ( ⁇ ) in the same manner as in Example 1 except that the compound represented by the formula (I) and the compound represented by the formula ( ⁇ ) were each changed to the compounds shown in Table 1 below. The formula compound was obtained. The chemical reaction formula at that time is shown in the following formula (7). Table 1 summarizes the yield of the heterocyclic compound represented by the formula (III).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne une méthode de production d'un composé hétérocyclique de formule (III) ci-dessous, où une imine aromatique réagit avec un aldéhyde. (Dans la formule, R1, R2, R3, R4, R5 et R7 représentent respectivement un atome d'hydrogène, un groupement alkyle, un groupement aryle, et similaires ; et X représente O, S, Se ou Te.) Ainsi, un isobenzofuranne et des composés similaires peuvent être synthétisés à partir d'un produit de départ aisément disponible via un procédé réactionnel court.
PCT/JP2007/054644 2006-03-10 2007-03-09 Méthode de production d'un composé hétérocyclique WO2007105622A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008222612A (ja) * 2007-03-09 2008-09-25 Okayama Univ イミノ基又はカルボニル基を含有する化合物の製造方法
JP2015119186A (ja) * 2008-09-25 2015-06-25 ユニバーサル ディスプレイ コーポレイション 有機セレン材料および有機発光デバイス内でのその使用

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CAVA M.P. ET AL.: "Condensed Cyclobutane Aromatic Compounds. XIII. An Attempted Synthesis of 1,2-Diphenylbenzocyclobutene", JOURNAL OF ORGANIC CHEMISTRY, vol. 25, no. 9, 1960, pages 1481 - 1484, XP003017749 *
JOHANSSON E. AND SKRAMSTAD J.: "Air Oxidation of an Isoindene: Formation of Isobenzofuran and Acetone", JOURNAL OF ORGANIC CHEMISTRY, vol. 46, no. 18, 28 August 1981 (1981-08-28), pages 3752 - 3754, XP003017750 *
KUNINOBU Y. ET AL.: "Insertion of Polar and Nonpolar Unsaturated Molecules into Carbon-Rhenium Bonds Generated by C-H Bond Activation: Synthesis of Phthalimidine and Indense Derivatives", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 1, 11 January 2006 (2006-01-11), pages 202 - 209, XP003017752 *
MOHANAKRISHNAN A.K. AND AMALADASS P.: "Synthesis of 1,3-Diarylbenzo[c]selenophenes", TETRAHEDRON LETTERS, vol. 46, no. 42, 17 October 2005 (2005-10-17), pages 7201 - 7204, XP005077518 *
MOHANAKRISHNAN A.K. AND AMALADASS P.: "Synthesis of 1,3-Diarylbenzo[c]thiophenes", TETRAHEDRON LETTERS, vol. 46, no. 24, 13 June 2005 (2005-06-13), pages 4225 - 4229, XP004890136 *
SHARP J.T. AND SKINNER C.E.D.: "The Generation and Reactions of C,N-dianions of Aromatic Tosylhydrazones: ortho-N-Dilithiated Benzophenone Tosylhydrazone", TETRAHEDRON LETTERS, vol. 27, no. 7, 1986, pages 869 - 872, XP003017751 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008222612A (ja) * 2007-03-09 2008-09-25 Okayama Univ イミノ基又はカルボニル基を含有する化合物の製造方法
JP2015119186A (ja) * 2008-09-25 2015-06-25 ユニバーサル ディスプレイ コーポレイション 有機セレン材料および有機発光デバイス内でのその使用

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