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Synthesis 2009(18): 3029-3038  
DOI: 10.1055/s-0029-1217604
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© Georg Thieme Verlag Stuttgart ˙ New York

Iodocyclization of N-[2-(Methylthio)phenyl]propiolamides: Selective Synthesis of 3-Iodo-1,5-benzothiazepin-4-ones

Tao-Shan Jiang, Xing-Guo Zhang, Jin-Heng Li*
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, P. R. of China
Fax: +86(731)8872101; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 19 March 2009
Publication Date:
10 July 2009 (online)

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Abstract

A selective method for the synthesis of 3-iodo-1,5-benzothiazepin-4-ones via the intramolecular iodocyclization of N-[2-(methylthio)phenyl]propiolamides has been developed. In the presence of I2, iodocyclizations of N-[2-(methylthio)phenyl]propiolamides were conducted smoothly to afford the corresponding 3-iodo-1,5-benzothiazepin-4-ones in moderate to good yields.

Key words

iodine - iodide - iodocyclization - N-[2-(methylthio)phenyl]propiolamide - 3-iodo-1,5-benzothiazepin-4-one