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Synthesis 2015; 47(22): 3593-3610
DOI: 10.1055/s-0034-1378805
DOI: 10.1055/s-0034-1378805
paper
Further Developments in the Reaction of 2-Aza-1,3,5-trienes with Superbases: Competitive Formation of New 4,5-Dihydro-1,3-thiazoles, Dihydroazepines, and Azepines by Tandem Deprotonation–Cyclization
Further Information
Publication History
Received: 08 May 2015
Accepted after revision: 05 June 2015
Publication Date:
03 August 2015 (online)
Abstract
Allyl- and benzylsulfanyl-substituted 2-aza-1,3,5-trienes, which are readily available from alkoxyallenes, isothiocyanates, and allyl or benzyl bromide, are easily transformed into polyfunctionalized 4,5-dihydro-1,3-thiazoles (2-thiazolines) through deprotonation of the activated SCH2 group upon treatment with superbase, followed by intramolecular [1,5]-ring-closing. Competitive deprotonation of the methyl group or methylene fragment of the ketimine function of the same molecule, followed by [1,7]-electrocyclization, leads to seven-membered azaheterocycles, dihydroazepines and/or azepines.
Key words
allenes - isothiocyanates - superbases - carbanions - intramolecular cyclizations - azepines, 2-thiazolinesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378805.
- Supporting Information
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