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Microwave-assisted synthesis of optically active N-substituted 2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and -thiazin-3(4H)-ones via Smiles rearrangement

Authors Meng L, Zuo H, Li Z, Dupati G, Jang K, Moon G, Zhao B, Miao J, Shin D

Received 18 May 2012

Accepted for publication 22 September 2012

Published 21 May 2013 Volume 2013:3 Pages 11—20


Checked for plagiarism Yes

Review by Single-blind

Peer reviewer comments 5

Li-Juan Meng,1 Hua Zuo,2 Zhu-Bo Li,2 Gautam Dupati,1 Kiwan Jang,1 Gichuel Moon,1 Bao-Xiang Zhao,3 Jun-Ying Miao,3 Dong-Soo Shin1

1Departments of Chemistry and Physics, Changwon National University, Changwon, South Korea; 2College of Pharmaceutical Sciences, Southwest University, Chongqing, People’s Republic of China; 3Institutes of Organic Chemistry and Developmental Biology, Shandong University, Jinan, People's Republic of China

Abstract: Optically active N-substituted-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and N-substituted-2-methyl-2H-benzo[b][1,4]thiazin-3(4H)-ones with potential synthetic and pharmacological interest were prepared via Smiles rearrangement using microwave irradiation in one-pot from inexpensive (S)-2-chloropropionic acid.

Keywords: microwave-assisted synthesis, Smiles rearrangement, optically active oxazinones, chiral thiazinones

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