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1. Reaction of dicyanomethylides with 3-(3′,3′-dimethyltriazene-1-yl)- pyridine-4-carboxylic acid. Unexpected preferential formation of pyrido[4,3-a]indolizines

Author

Takane Uchida, Mituo Toda, J. William Lown, Akikazu Kakehi, Kinuyo Aoyama, Atsushi Shigihara, and Kiyoshi Matsumoto

Subjects
chemistry.chemical_classification, Stereochemistry, Carboxylic acid, Organic Chemistry, Azomethine ylide, Regioselectivity, Crystal structure, Biochemistry, Medicinal chemistry, chemistry.chemical_compound, Atomic orbital, chemistry, Drug Discovery, Pyridine, X-ray crystallography, Molecule
Abstract

Contrary to theoretical predictions on the basis of a discrete hetaryne intermediate (frontier orbitals, total atomic charges on C-3 and C-4, and activation energies for the concerted process) from the MO calculations, reactions of dicyanomethylides with 3-(3′,3′-dimethyltriazene-1-yl)pyridine-4-carboxylic acid, a formal precursor of 3,4-didehydropyridine, afforded exclusively the pyrido[4,3-a]indolizines. The results are better in accord with a mechanism involving a zwitterionic hetaryne precursor.

Published
1992

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