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New Reagent for Convenient Access to the α,β‐Unsaturated N ‐Methoxy‐ N ‐methyl‐amide Functionality by a Synthesis Based on the Julia Olefination Protocol
Author(s) -
Narayana Manjunath Beedimane,
Sane Neeraj P.,
Singh Aidhen Indrapal
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600126
Subject(s) - chemistry , reagent , amide , organic chemistry , combinatorial chemistry , stereochemistry
A new reagent for the synthesis of the α,β‐unsaturated N ‐methoxy‐ N ‐methyl‐amide structural unit has been developed. 2‐(Benzo[ d ]thiazol‐2‐ylsulfonyl)‐ N ‐methoxy‐ N ‐methylacetamide, a crystalline solid with an indefinite shelf life that can be easily prepared in two convenient steps from 2‐chloro‐ N ‐methoxy‐ N ‐methylacetamide, reacted with a variety of aldehydes under Julia conditions to furnish the α,β‐unsaturated N ‐methoxy‐ N ‐methyl‐amide functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)