NL2015814B1 - Pyridine-based isocyanides as novel reagents for multicomponent reactions. - Google Patents

Pyridine-based isocyanides as novel reagents for multicomponent reactions. Download PDF

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Publication number
NL2015814B1
NL2015814B1 NL2015814A NL2015814A NL2015814B1 NL 2015814 B1 NL2015814 B1 NL 2015814B1 NL 2015814 A NL2015814 A NL 2015814A NL 2015814 A NL2015814 A NL 2015814A NL 2015814 B1 NL2015814 B1 NL 2015814B1
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NL
Netherlands
Prior art keywords
group
isocyanopyridines
isocyanopyridine
substituted
nmr
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Application number
NL2015814A
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English (en)
Inventor
Van Der Heijden Gydo
Adrianus Wilhelmus Jong Jacobus
Vincenzo Antonio Orru Romano
Ruijter Eelco
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Stichting Vu-Vumc
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Priority to NL2015814A priority Critical patent/NL2015814B1/en
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Publication of NL2015814B1 publication Critical patent/NL2015814B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Claims (20)

1. Methode voor het uitvoeren van isocyanide gebaseerde multicomponent reactie (IMCR) bestaande uit een stap van het laten reageren van een gesubstitueerd 2 - of 4-isocyanopyridine van de algemene formule 5 of 19, bij voorkeur 5,
5 19 met een carbonyl-bevattende stof geselecteerd uit de groep bestaande een aldehyde of een keton; in aanwezigheid van een zure koolstof verbinding geselecteerd uit de groep bestaande uit een (thio) carbonzuur en een (thio) fenolische verbinding en/of een primair of secundair amine, waarin R wordt geselecteerd uit de groep bestaande uit H, halogeen, C1-C4-alkyl zoals Cr, C2-, n-C3-, /'-C3- alkyl gehalogeneerde C1-C4 alkyl, halogeen (F, Cl, Br, I), (thio) ethers, sulfoxiden, sulfonen , esters, (gesubstitueerd) (hetero) aryl, (gesubstitueerd) cycloalkyl, alkoxy / (hetero) aryloxy en mono-di-alkyl / (hetero) arylamino.
2. De methode volgens conclusie 1, waarin de zure koolstof verbinding een carbonzuur is (Passerini reactie).
3. De methode volgens conclusie 1, waarin verder een primair amine aanwezig is (Ugi reactie
4. De methode volgens conclusie 1, waarin de zure koolstof verbinding een fenolische verbinding is (Ugi-Smiles reactie).
5. De methode volgens conclusie 1, waarin R gelegen is op de 3, 4, 5 of 6 positie in de 2-isocyanopyridine of waarin R gelegen is op de 2, 3, 5 of 6 positie in de 4-isocyanopyridine.
6. Methode volgens conclusie 1, waarin R is geselecteerd uit de groep bestaande uit Cr, C2-, n-C3-, /'-C3- alkyl, halogeen (F, Cl, Br, I), CF3.
7. De methode volgens conclusie 6, waarin, voor 2-isocyanopyridines, R is geselecteerd uit de groep bestaande uit 3-Me, 4-Me, 5-Me, 6-Me, 3-Br, 4-Br, 5-Br, 6-Br, 3-CI, 4-CI, 5-CI, 6-CI, 3-F, 4-F, 5-F, 6-F, 3-CF3, 4-CF3,5-CF3,6-CF3 en waarin voor4-isocyanopyridines , R is geselecteerd uit de groep bestaande uit -Me, 3-Me, 5-Me, 6-Me, 2-Br, 3-Br, 5-Br, 6-Br, 2-CI, 3-CI, 5-CI, 6-CI, 2-F, 3-F, 5-F, 6-F, 2-CF3,3-CF3, 5-CF3,6-CF3.
8. De methode volgens conclusie 7, waarin, voor 2-isocyanopyridines, R is geselecteerd uit de groep bestaande uit 3-Me, 4-Me, 5-Me, 6-Me, 3-Br, 4-Br, 5-Br, 5-CI, 5-CF3, 6-Br, 6-Cl.
9. De methode volgens conclusie 8, waarin R is Br, bij voorkeur 6-Br.
10. Gesubstitueerde 2-isocyanopyridine of 4-isocyanopyridine met de algemene formule or
5 19 waarin R is geselecteerd uit de groep bestaande uit H, Ci-C4-alkyl such as Cr, C2-, n-C3-, i-C3- alkyl, gehalogeneerde C1-C4 alkyl, halogeen (F, Cl, Br, I), (thio)ethers, sulfoxides, sulfonen, esters, (gesubstitueerde) (hetero)aryl, (gesubstitueerde) cycloalkyl, alkoxy/(hetero)aryloxy, en mono-di-alkyl/(hetero)arylamino.
11. Gesubstitueerde 2-isocyanopyridine of 4-isocyanopyridine volgens conclusie 10, waarin voor 2-isocyanopyridines, R is geselecteerd uit de groep bestaande uit 3-Me, 4-Me, 5-Me, 6-Me, 3-Br, 4-Br, 5-Br, 6-Br, 3-CI, 4-CI, 5-CI, 6-CI, 3-F, 4-f, 5-F, 6-F, 3-CF3, 4-CF3,5-CF3, 6-CF3 en waarin voor 4-isocyanopyridines, R is geselecteerd uit de groep bestaande uit, 3-Me, 2-Br, 3-Br, 2-CI, 3-CI, 2-F, 3-F, 2-CF3, 3-CF3.
12. Gesubstitueerde 2-isocyanopyridine of 4-isocyanopyridine volgens conclusie 11, waarin voor 2-isocyanopyridines, R is geselecteerd uit de groep bestaande uit 3-Me, 4-Me, 5-Me, 6-Me, 3-Br, 4-Br, 5-CF3, 6-Br, 6-CI en waarin voor 4-isocyanopyridines R is geselecteerd uit de groep bestaande uit 2-Me, 2-Br, 2-CF3, 2-CI.
13. Gesubstitueerde 2-isocyanopyridine of 4-isocyanopyridine volgens conclusie 12, waarin voor 2-isocyanopyridines R is Br, bij voorkeur 6-Br en waarin voor 4-isocyanopyridines R is Br of Cl , bij voorkeur 2-Br of 2-CI.
14. Methode voor de omzetting van de N-2-pyridylamide - of N-4-pyridylamide-bevattende product van de Ugi reactie van conclusie 3 tot de overeenkomstige carbonzuur onder basische condities.
15. Methode voor de nucleofiele substitutie van de N-2-pyridylamide of N-4-pyridylamide-groep van het N-2-pyridylamide - of N-4-pyridylamide- product van de Ugi reactie van conclusie 3 in aanwezigheid van een nucleofiel onder zure of basische condities.
16. De methode volgens conclusie 15, waarin het nucleofiel is geselecteerd uit de groep bestaande uit water, alcoholen, thiolen, primaire of secundaire amines.
17. Methode volgens conclusie 15 of 16, waarin de condities basisch zijn en het nucleofiel is geselecteerd uit de groep bestaande uit water, primaire CrC4-alcoholen, primaire CrC8 alkylaminen, secundaire C2-C8 alkylaminen en C4-C8 cycloalkylamines.
18. Methode volgens conclusie 15 of 16, waarin de voorwaarden zuur zijn en het nucleofiel is geselecteerd uit de groep bestaande uit water, primaire Ci-C4-alcoholen, secundaire C3-C8-alcoholen, alkylthiolen, benzylthiolen.
19. Methode voor de omzetting van het N-2-pyridylamide - of N-4-pyridylamide- product van de Passerini reactie van conclusie 2 onder basische condities om het overeenkomstige alpha-hydroxy carbonzuur te verkrijgen.
20. Toepassing van gesubstitueerde 2-isocyanopyridines of gesubstitueerde 4-isocyanopyridines zoals gedefinieerd in conclusie 10 in multicomponent reacties.
NL2015814A 2015-11-19 2015-11-19 Pyridine-based isocyanides as novel reagents for multicomponent reactions. NL2015814B1 (en)

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NL2015814A NL2015814B1 (en) 2015-11-19 2015-11-19 Pyridine-based isocyanides as novel reagents for multicomponent reactions.

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NL2015814A NL2015814B1 (en) 2015-11-19 2015-11-19 Pyridine-based isocyanides as novel reagents for multicomponent reactions.

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3719424A1 (de) * 1987-06-11 1988-12-22 Merck Patent Gmbh Fluessigkristalline isocyanate
EP2590953A1 (en) * 2010-07-09 2013-05-15 Convergence Pharmaceuticals Limited Tetrazole compounds as calcium channel blockers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3719424A1 (de) * 1987-06-11 1988-12-22 Merck Patent Gmbh Fluessigkristalline isocyanate
EP2590953A1 (en) * 2010-07-09 2013-05-15 Convergence Pharmaceuticals Limited Tetrazole compounds as calcium channel blockers

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DÖMLING ET AL.: "Chemistry and Biology of Multicomponent Reactions", CHEMICAL REVIEWS, vol. 112, 2012, pages 3083 - 3135, XP002760357 *
GUO ET AL.: "Transition metal complexes of isocyanopyridines, isocyanoquinolines and isocyanoisoquinolines", INORGANICA CHIMICA ACTA, vol. 261, 1997, pages 141 - 146, XP002760355 *
JIANG ET AL.: "Synthesis of 6-Alkylated Phenanthridine Derivatives Using Photoredox Neutral Somophilic Isocyanide Insertion", ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 13289 - 13292, XP002760356 *
SHAO N ET AL: "Dimerization of 2-pyridylisonitriles produces pi-extended fused heteroarenes useful as highly selective colorimetric and optical probes for copper ion", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 66, no. 36, 4 September 2010 (2010-09-04), pages 7302 - 7308, XP027205684, ISSN: 0040-4020, [retrieved on 20100801] *

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