Multi component coupling reactions of N-acetyl-2-azetine

Paul Stevenson, Mark Nieuwenhuyzen, D. Osborne

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

N-Acetyl-2-azetine undergoes Lewis acid catalysed formal [4+2]-cycloaddition with imines derived from aromatic amines to initially give an approximately 1: 1 mixture of exo-endo-diastereoisomeric 1-(2a,3,4,8b-tetrahydro-2H-1,4-diaza-cyclobuta[a]naphthalen-1-yl)-ethanone cycloadducts which were detected by proton NMR spectroscopy. These products, which were too unstable to isolate, and characterise, reacted further with aromatic amines to give 2,3,4-trisubstituted tetrahydroquinolines in good to excellent yield, predominantly as a single diastereoisomer, with the minor diastereoisomer converting to the major diastereoisomer on silica. The cycloaddition was irreversible and a mechanism is presented for the formation of the major diastereoisomer from the mixture of diastereoisomeric intermediates. A range of conditions is described for converting the 2,3,4-trisubsitituted tetrahydroquinolines into 2,3-disubstituted quinolines.
Original languageEnglish
Pages (from-to)129-144
Number of pages16
JournalArkivoc
Volume11
Issue number11
Publication statusPublished - 2007

ASJC Scopus subject areas

  • Organic Chemistry

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