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The reaction of 2-dimethylaminomethylene-3-oxo-N-phenylbutyramide with active methylene nitriles

✍ Scribed by Fathy M. Abdelrazek; Mohey F. Sharaf; Peter Metz; Anna Jaeger

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
155 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

2‐Dimethylaminomethylene‐3‐oxo‐N‐phenylbutyramide 1 reacts with malononitrile 2a to afford the pent‐2‐enedioic acid 1‐amide 5‐phenylamide derivative 6, which could be cyclized to give the 6‐methylpyridone derivative 7. Compound 1 reacts with cyanoacetamide 2b to afford the same pyridone 7 and with cyanothioacetamide 2c to afford the analogous pyridinethione 12. Compound 12 reacts with DMAD to afford the pyridine derivative 15 and with N,N‐dimethylchloroacetamide 16 to afford the thieno[2,3‐d]pyridine derivative 18. Compound 18 reacts with morpholine‐4‐carboxaldehyde 19, N,N‐diemthylformamide 20, and 2,5‐dimethoxy‐tetrahydrofuran 21 to afford the fully aromatic thieno[2,3‐d]pyridine derivatives 22, 23, and 24, respectively. J. Heterocyclic Chem., (2010).

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