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Heterocyclic Compounds with a Bridge Nitrogen Atom. 14. Cycloaddition of Acetylenedicarboxylic Acid Ester to 2-Chloro-N-phenacylpyridinium Ylide. Crystal Structure of Dimethyl Ester of 5-Chloro-3-(p-nitrobenzoyl)indolizine-1,2-dicarboxylic Acid |
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| Authors: | E. V. Babaev K. Yu. Pasichnichenko V. B. Rybakov S. G. Zhukov |
| Affiliation: | (1) M. V. Lomonosov Moscow State University, Moscow, 119899, Russia |
| Abstract: | Derivative of 5-chloroindolizine is formed in the reaction of 2-chloro-1-(p-nitrophenacyl)pyridinium ylide with acetylenedicarboxylic acid dimethyl ester, the structure of which was demonstrated by X-ray diffraction analysis. According to data of 1H NMR and mass spectra indolizine obtained undergoes an unusual intramolecular cyclization with the formation of benz[e]cycl[3.3.2]azine nucleus. |
| Keywords: | benz[e]cycl[3.3.2]azine acetylenedicarboxylic acid dimethyl ester condensed heterocycles indolizine pyridine pyridinium ylide pyrrole 5-chloroindolizine 2-chloro-1-(p-nitrophenacyl)-pyridinium bromide intramolecular cyclization of 3-aroyl-5-chloroindolizines 1,3-dipolar cycloaddition X-ray diffraction analysis |
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