Synlett 2018; 29(12): 1649-1653
DOI: 10.1055/s-0037-1610171
letter
© Georg Thieme Verlag Stuttgart · New York

Vinylogous Blaise Reaction: Conceptually New Synthesis of Pyridin-2-ones

H. Surya Prakash Rao*
Department of Chemistry, Pondicherry University, Pondicherry-605 014, India
,
Nandurka Muthanna
Department of Chemistry, Pondicherry University, Pondicherry-605 014, India
,
Ashiq Hussain Padder
Department of Chemistry, Pondicherry University, Pondicherry-605 014, India
› Author Affiliations

H.S.P.R. thanks the University Grants Commission (UGC), the Major Research Project (MRP) Special Assistance Program (SAP), and the ­Department of Science and Technology Fund for Improvement of S&T Infrastructure in Universities and Higher Educational Institutions (DST-FIST) programs. N.M. thanks the UGC for a fellowship. A.H.P. thanks Pondicherry University for a fellowship. The authors thank the Central Instrumentation Facility (CIF) and Department of Chemistry for the instrumentation facilities.
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Publication History

Received: 12 April 2018

Accepted after revision: 13 May 2018

Publication Date:
19 June 2018 (online)


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Abstract

A conceptually new synthesis of pyridine rings by a [C4 + CN] assembly has been developed by applying a vinylogous version of the classic Blaise reaction. The zinc-mediated reaction of (het)aryl or alkyl nitriles with ethyl-4-bromocrotonate provided a variety of C(6)-substituted pyridin-2-ones in a single-step.

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