[5C+1N] Annulation:A Facile Synthetic Strategy Toward Substituted Pyridin-4(1H)-ones

doi:10.3724/SP.J.1095.2012.20146

Chinese Journal of Applied Chemistry

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[5C+1N] Annulation:A Facile Synthetic Strategy Toward Substituted Pyridin-4(1H)-ones

OUYANG Yan¹, ZHANG Rui², HE Xiaoyan¹, HUANG Jie², ZHANG Yuemei¹, DONG Dewen^2,3*

(1.College of Chemistry and Biological Sciences,Yili Normal University,Yining 835000，China;
2.Green Chemistry and Process Laboratory,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022，China;
3.Changzhou Institute of Energy Storage Materials & Devices,Chinese Academy of Sciences,Changzhou 213000,China)

Received:2012-04-11 Revised:2012-05-17 Published:2012-09-10 Online:2012-09-10
Contact: DONG Dewen

Abstract

Abstract: A facile synthesis of substituted pyridin-4(1H)-ones from readily available α-(N,N-dimethylamino)-alkenoyl ketene-S,S-acetals and aliphatic amines has been developed. Substituted pyridin-4(1H)-ones were synthesized via a formal [5C+1N] annulation of α-(N,N-dimethylamino)-alkenoyl ketene-S,S-acetals in N,N-dimethylformamide at 60 ℃. An intramolecular azanucleophilic vinyl substitution reaction occurs to give the corresponding pyridin-4(1H)-ones in high yields(75%~95%).

Key words: aza-heterocycles, &, alpha, -(N,N-dimethylamino)-alkenoyl ketene-S,S-acetals, [5C+1N] annulation, pyridin-4(1H)-ones

CLC Number:

O621

OUYANG Yan1 ZHANG Rui2 HE Xiaoyan1 HUANG Jie2 ZHANG Yuemei1 DONG Dewen2,3*. [5C+1N] Annulation:A Facile Synthetic Strategy Toward Substituted Pyridin-4(1H)-ones[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2012.20146.

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[5C+1N] Annulation:A Facile Synthetic Strategy Toward Substituted Pyridin-4(1H)-ones

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