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-(<i>p</i>-NITROBENZOYL)INDOLIZINE-1,2-DICARBOXYLIC ACID

Authors

  • Е. В. Бабаев M. V. Lomonosov Moscow State University
  • К. Ю. Пасичниченко M. V. Lomonosov Moscow State University
  • В. Б. Рыбаков M. V. Lomonosov Moscow State University
  • С. Г. Жуков M. V. Lomonosov Moscow State University

DOI:

https://doi.org/10.1007/390

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 analysi

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.

Authors: E. V. Babaev, K. Yu. Pasichnichenko, V. B. Rybakov, and S. G. Zhukov.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (10), pp 1192-1197

http://link.springer.com/article/10.1023/A%3A1002872800920

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Published

2013-03-14

Issue

No. 10 (2000)

Section

Original Papers