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Reaction of dicyanomethylides with 3-(3′,3′-dimethyltriazene-1-yl)- pyridine-4-carboxylic acid. Unexpected preferential formation of pyrido[4,3-a]indolizines
- Source :
- Tetrahedron Letters. 33:7643-7646
- Publication Year :
- 1992
- Publisher :
- Elsevier BV, 1992.
-
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.
Details
- ISSN :
- 00404039
- Volume :
- 33
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........e039488654c34a4a8198ae7df7d89741