GB1098355A - Method of preparation of dihydropyrrole derivatives - Google Patents

Method of preparation of dihydropyrrole derivatives

Info

Publication number
GB1098355A
GB1098355A GB5177964A GB5177964A GB1098355A GB 1098355 A GB1098355 A GB 1098355A GB 5177964 A GB5177964 A GB 5177964A GB 5177964 A GB5177964 A GB 5177964A GB 1098355 A GB1098355 A GB 1098355A
Authority
GB
United Kingdom
Prior art keywords
diphenyl
azlactone
methyl
dimethyl
pyrroline
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5177964A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB1098355A publication Critical patent/GB1098355A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/72—4,7-Endo-alkylene-iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dihydropyrroles of the general formula <FORM:1098355/C2/1> <FORM:1098355/C2/2> are obtained by contacting an olefinic compound of the formula (R)2C=C(R)2 with an azlactone or mesoionic azlactone of the respective general formula <FORM:1098355/C2/3> <FORM:1098355/C2/4> wherein each of R, R1, R2 and R3 represents hydrogen or monovalent aliphatic, cycloaliphatic, aromatic or heterocyclic groups attached to the ring atoms through a carbon to carbon bond or in the case when R3 is other than hydrogen through a carbon to nitrogen bond, also R may be cyano and R1 and R3 can together form an alkylene group, but in the reaction with a mesoionic azlactone at least one of the substituents R must be a hydrogen atom. The reactants are suitably contacted at between 0 DEG and 140 DEG C., preferably between 50 DEG and 140 DEG C., and the reaction is preferably carried out in an inert solvent, especially benzene, toluene, xylene or dioxane. The process may also be conducted in an inert atmosphere, e.g. of nitrogen or argon. The azlactone may be derived from an appropriate a -amino-carboxylic acid and the azlactone or mesionic azlactone is preferably formed in situ by starting with an appropriate a -amino carboxylic acid containing primary or secondary amino groups or its N-acyl derivative with the aid of an acid anhydride, e.g. acetic anhydride, and the resulting azlactone or mesoionic azlactone then reacts immediately with the unsaturated compound present as the other reactant. Substituents may be present on the various R to R3 groups and the group R1 may be any natural alpha-amino acid residue. Examples of the group R2 are methyl, ethyl, n-pentyl, isopropyl, cyclohexyl, phenyl, b -pyridyl, p-chlorophenyl, o-nitrophenyl, betanaphthyl and p-acetaminophenyl. The unsaturated reactant may be e.g. propylene, cyclopentene, 1-hexene, norbornene, styrene, acenaphthylene, stilbene, 1,2-dihydronaphthalene, indene, butadiene, isoprene, phenyl butadiene, chloroprene, a cinnamic, acrylic, fumaric, maleic or mesaconic ester, ethylenetetracarboxylic ester, benzalacetone, dibenzoylethylene, benzalacetophenone, acrylonitrile, methacrylonitrile, fumaric acid dinitrile, 1 - phenyl phenyl - 2 - nitroethylene or cinnamonitrile. Several examples are given and the invention also includes as new products compounds of the given general formulaae in which R, R1, R2 and R3 are as defined above with the proviso that (a) not more than two of the groups R, R1, R2 and R3 represent hydrogen, (b) R1 and R3 can also together form an alkylene group, and (c) when the ring nitrogen is unsubstituted then R1 and R2 must always be aryl. The invention also includes per se the following specific compounds which are products of certain of the examples: (1) dimethyl 2,5 - diphenyl - D 1 - pyrroline - 3,4 - dicarboxylate, (2) 2,5 - diphenyl - 3 - cyano-D 1-pyrroline, - 4 - carboxylate, (4) 1 - methyl - 2,3,3,5 - tetraphenyl (3) ethyl 2,3,5-triphenyl-D 1-pyrroline-4 - carboxylate, (4) 1 - methyl - 2,3,3,5 - tetraphenyl - 2,3 - dihydropyrrole, (5) dimethyl 1 - methyl - 2,5 - diphenyl - 2,3 - dihydropyrrole - 3,4 - dicarboxylate, (6) 1 - methyl-2,5-diphenyl - 3,4 - dibenzoyl - 2,3 - dihydrpyrrole, (7) methyl 1,4 - dimethyl - 2,5 - diphenyl-D 2-pyrroline - 3 - carboxylate, (8) dimethyl 1,4-dimethyl - 2,5 - diphenyl - D 2 - pyrroline - 3,4-dicarboxylate and (9) dimethyl 2,5-dimethyl-1 - cyclohexyl - D 2 - pyrroline - 3,4 - dicarboxylate. In one of the examples (Example 15), 1 - methyl - 2,5 - diphenyl - 3 - n - butylpyrrole is obtained by reacting anhydro-5-hydroxy-3-methyl-2,4-diphenyl-oxazolium hydroxide with n-hexene-(1), elimination of hydrogen occuring on working up the product.
GB5177964A 1963-12-20 1964-12-21 Method of preparation of dihydropyrrole derivatives Expired GB1098355A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEU0010358 1963-12-20

Publications (1)

Publication Number Publication Date
GB1098355A true GB1098355A (en) 1968-01-10

Family

ID=7567191

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5177964A Expired GB1098355A (en) 1963-12-20 1964-12-21 Method of preparation of dihydropyrrole derivatives

Country Status (2)

Country Link
DE (1) DE1470386A1 (en)
GB (1) GB1098355A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489490B1 (en) * 1998-05-18 2002-12-03 Bayer Aktiengesellschaft 2-(2-chlorophenyl)-3,4-dihydro-2h-pyrrol derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4687861A (en) * 1984-11-28 1987-08-18 Ciba-Geigy Corporation Microbicidal compositions
US5118816A (en) * 1990-12-26 1992-06-02 American Cyanamid Company 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489490B1 (en) * 1998-05-18 2002-12-03 Bayer Aktiengesellschaft 2-(2-chlorophenyl)-3,4-dihydro-2h-pyrrol derivatives

Also Published As

Publication number Publication date
DE1470386A1 (en) 1969-05-29

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