Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 60, No. 8, 2003, pp.1855-1864
Published online, 15th July, 2003
DOI: 10.3987/COM-03-9809
Synthesis of 1,2-Benzisothiazolin-3-one by Transamination of Sulfenamides

Masao Shimizu,* Ayanobu Takeda, Hidenori Fukazawa, Yoshimoto Abe, and Isao Shibuya

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan

Abstract

N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on the sulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones by intramolecular transamination was also investigated by S-amination of 2-mercaptobenzamides.