Issue 34, 2011
From the journal:

Chemical Communications

Synthesis of 4-methylene-4H-benzo[d][1,3]thiazines via a tandem reaction of 1-(2-alkynylphenyl)ketoximes with Lawesson's reagent†

Guanyinsheng Qiu,a   Yi Hu,a   Qiuping Ding,a   Yiyuan Peng,*a   Xiangzheng Huc  and  Jie Wu*b  

* Corresponding authors

a Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China

b Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
E-mail: jie_wu@fudan.edu.cn
Fax: +86 21 6564 1740
Tel: +86 21 6510 2412

c College of Science, Tianjin University of Science and Technology, Tianjin 300222, China

Abstract

1-(2-Alkynylphenyl)ketoximes react with Lawesson's reagent catalyzed by InCl3 and cyanuric chloride leading to 4-methylene-4H-benzo[d][1,3]thiazines in good yields. This tandem reaction proceeds with high efficiency through Beckmann rearrangement, thioamide formation, and intramolecular nucleophilic cyclization.

Graphical abstract: Synthesis of 4-methylene-4H-benzo[d][1,3]thiazines via a tandem reaction of 1-(2-alkynylphenyl)ketoximes with Lawesson's reagent

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Article information

DOI
https://doi.org/10.1039/C1CC12937F
Article type
Communication
Submitted
19 May 2011
Accepted
14 Jul 2011
First published
27 Jul 2011

Chem. Commun., 2011,47, 9708-9710

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Synthesis of 4-methylene-4H-benzo[d][1,3]thiazines via a tandem reaction of 1-(2-alkynylphenyl)ketoximes with Lawesson's reagent

G. Qiu, Y. Hu, Q. Ding, Y. Peng, X. Hu and J. Wu, Chem. Commun., 2011, 47, 9708 DOI: 10.1039/C1CC12937F

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