Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals

A new strategy for the synthesis of 2,3,5-trisbustituted furans from α-formylketene dithioacetals is described. The protocol involves a facile conversion of α-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-t...

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Bibliographic Details
Published in:Tetrahedron letters 2011-04, Vol.52 (14), p.1667-1669
Main Authors: Sasikala, K.A., Kalesh, K.A., Anabha, E.R., Pillai, P. Madhavan, Asokan, C.V., Devaky, K.S.
Format: Article
Language:English
Subjects:
Bromination
Chemistry
Conversion
Exact sciences and technology
Furan
Furans
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
N-Bromosuccinimide
Organic chemistry
Preparations and properties
Strategy
Synthesis (chemistry)
Tetrahedrons
Utilities
Vinylketene dithioacetal
α-Formylketene dithioacetal
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Summary:A new strategy for the synthesis of 2,3,5-trisbustituted furans from α-formylketene dithioacetals is described. The protocol involves a facile conversion of α-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.01.128