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FeCI3-promoted [3+3] cycloaddition: Efficient preparation of 1,2-dihydro-2-oxo-3-pyridinecarboxylate and 1,2-dihydro-2-oxo-3-pyridinecarboxamide derivatives

✍ Scribed by Shuheng Li; Shaozhong Wang

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 176 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450651

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✦ Synopsis

Abstract

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A facile approach was developed on assembly of the 2‐pyridone nucleus by ferric chloride promoted [3+3] cycloaddition in propionic acid. The tandem process involves cyclization of Michael adduct followed by aromatization. Thus, different substituted 1,2‐dihydro‐2‐oxo‐3‐pyridinecarboxylate and 1,2‐dihydro‐2‐oxo‐3‐pyridinecarboxamide derivatives were prepared in good yields from various enones with malonamic ester and malonamide, respectively

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