Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process

Zsolt Szakonyi, Ferenc Fülöp, Dirk Tourwé, Norbert De Kimpe

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.

Original languageEnglish
Pages (from-to)2192-2196
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number7
DOIs
Publication statusPublished - Apr 5 2002

ASJC Scopus subject areas

  • Organic Chemistry

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