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ChemInform Abstract: Synthesis via 2-Acylmethyl-2-oxazoline. Part 1. A Novel Synthesis of 3-Acyl-2-pyridones by Michael Addition of 2-Acylmethyl-2-oxazoline to α,β-Acetylenic Ketones.

✍ Scribed by Y. TOHDA; T. YANAGIDANI; S. HIRAMATSU; N. NISHIWAKI; K. TANI; K. IMAGAWA; M. ARIGA

Publisher: John Wiley and Sons
Year: 2010
Weight: 47 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199811156

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✦ Synopsis

Synthesis via 2-Acylmethyl-2-oxazoline. Part 1. A Novel Synthesis of 3-Acyl-2-pyridones by Michael Addition of 2-Acylmethyl-2-oxazoline to α,β-Acetylenic Ketones.

-The title reaction is studied and some conversions of the acyl-pyridones, such as (IV) and (V) are investigated, e.g. deacylation yielding products like (VII) and N-dealkylation giving compounds such as (VIII). The reaction mechanisms are discussed. The desired title products are obtained directly from the reaction of oxazolines (I) with α,βacetylenic ketones after treatment of the primary adducts with SiO 2 . Further transformations are studied and found to be dependent on the N-tertiary alkyl substituent. -(TOHDA, Y.

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