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Enamine reactivity of 3-(l-pyrrolidinyl)heteroaromatics: Reactions with ketenes and nitro-olefines

✍ Scribed by H. C. Mutreja; D. N. Reinhoudt

Book ID: 104588246
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 713 KB
Volume: 99
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19800990706

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✦ Synopsis

Abstract

Ketenes react with 1‐pyrrolidinyl‐substituted heteroaromatics 3‐5 to give 2‐acyl derivatives 10, 13, 16‐18 and 20 and, in some cases 2: 1 reaction products 11 and 12. The latter products can be attributed to reaction of 1,4‐dipolar intermediates with a second molecule of ketene. With β‐nitro‐styrene, compounds 4b and 5 give only the corresponding 2‐alkyl‐substituted products 21 and 22, respectively. These reactions further demonstrate the “enamine‐like” character of 3‐(1 ‐pyrrolidinyl)‐substituted heteroaromatics 3‐5.

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