Preparation of cycloalkano[c]pyridazinones and cycloalkane-condensed pyrrolo[1,2-a]imidazolone, -pyrimidinone and -[1,3]diazepinone stereoisomers

Ferenc Csende, Gábor Bernáth, Zsolt Böcskei, Pál Sohár, Géza Stájer

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11 Citations (Scopus)

Abstract

From the 2-ethoxycarbonylmethyl-1-cycloalkanones (1a-c) with hydrazine, the cyclopenta- (2a), cyclohexa- (2b) and cyclohepta[c]pyridazinones (2c) were prepared. 2a-c were transformed to the corresponding dehydro derivatives (3a-c) by means of a recently-developed smooth oxidation method with CuCl2 in acetonitrile. Compounds (1) reacted with α,ω-alkylenediamines to furnish saturated cycloalkano[6]pyrrolo[1,2-cr]diazinones (4a-f). The structures of 4a-f were determined by 1H- and 13C-NMR methods, including DNOE, DEPT and 2D-HSC measurements, and for 4a also by X-ray analysis. The rings of the 2-perhydroindolone and its homologues are cis-fused, while the NH group of the heterocycle containing two N atoms and the annelational hydrogen are cis in all compounds prepared.

Original languageEnglish
Pages (from-to)323-330
Number of pages8
JournalHeterocycles
Volume45
Issue number2
DOIs
Publication statusPublished - Jan 1 1997

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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