PBr3-mediated [5 + 1] annulation of α-alkenoyl-α-carbamoyl ketene-S,S-acetals: access to substituted pyridine-2,6(1H,3H)-diones

Liping Shi; Qian Zhang; Fengjiao Gan; Rui Zhang; Yuanli Ding; Chun Liu; Dewen Dong

doi:10.1039/C5RA13498F

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PBr₃-mediated [5 + 1] annulation of α-alkenoyl-α-carbamoyl ketene-S,S-acetals: access to substituted pyridine-2,6(1H,3H)-diones†

Liping Shi,^a Qian Zhang,^b Fengjiao Gan,^b Rui Zhang,*^b Yuanli Ding,^b Chun Liu^a and Dewen Dong*^b

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* Corresponding authors

^a College of Chemistry and Biology, Beihua University, Jilin, China

^b Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
E-mail: ariel@ciac.ac.cn, dwdong@ciac.ac.cn

Abstract

A facile and efficient synthesis of substituted pyridine-2,6(1H,3H)-diones via an intramolecular [5 + 1] annulation of readily available α-alkenoyl-α-carbamoyl ketene-S,S-acetals mediated by phosphorus bromide (PBr₃) under very mild conditions is described.

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Article information

DOI: https://doi.org/10.1039/C5RA13498F
Article type: Paper
Submitted: 10 Jul 2015
Accepted: 23 Sep 2015
First published: 24 Sep 2015

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RSC Adv., 2015,5, 82743-82747

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PBr₃-mediated [5 + 1] annulation of α-alkenoyl-α-carbamoyl ketene-S,S-acetals: access to substituted pyridine-2,6(1H,3H)-diones

L. Shi, Q. Zhang, F. Gan, R. Zhang, Y. Ding, C. Liu and D. Dong, RSC Adv., 2015, 5, 82743 DOI: 10.1039/C5RA13498F

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