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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 12
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Original Articles

The Synthesis of Aminobenzothiazoles from 2,3-Biaryl-5-anilino-Δ3-1,2,4-thiadiazolines

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Pages 2053-2060 | Received 01 Oct 2002, Published online: 17 Aug 2006
 

Abstract

2-Amidinobenzothiazoles 4 can be prepared in high yields by a thermally-promoted rearrangement of thiadiazolium salts 1 or thiadiazolines 2. Addition of base to the rearrangement of the thiadiazolium salts can improve the yields by the prior conversion of the thiadiazolium salts to the corresponding thiadiazoline free bases. The rearrangement of the thiadiazolines may go through an electrophilic aromatic substitution or free radical pathway.

Acknowledgment

The authors would like to thank Dr. Dennis Hlasta for useful discussions, support, and encouragement, and Diane Gauthier for performing many of the NMR experiments.

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