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:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 65, No. 7, 2005, pp.1615-1627
Published online, 28th April, 2005
DOI: 10.3987/COM-05-10414
Facile Synthesis of 2-Substituted 4H-1,3-thiazines and 3-Substituted 1,2-Isothiazoles via Benzyne Intermediates

Ramadas Sathunuru, Hongming Zhang, Chrles W. Rees, and Edward Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.


Substituted 2-dialkylamino-4H-1,3-benzothiazines were Synthesizedby the reaction of (phenyl)[o-(trimethylsilyl)aryl]iodonium triflates and dialkyl-aminothiazadienes in the presence of 1.5 equivalent of Bu4NF. However, when these reactions were carried out in the presence of 4 equivalents of Bu4NF, 3-substituted 1,2-benzisothiazoles were obtained. Additionally, the reaction of phenyl[(3-trimethylsilyl)-2-naphthyl]iodonium triflate with dialkylaminothia-zadienes in the presence of Bu4NF gave 3-substituted 1,2-naphthisothiazoles. A possible mechaism for the latter reaction involving the trapping of a benzyne intermediate with a nitrile sulfide generated in situ by the reaction of dialkylaminothiazadiene, fluoride ion and trimethylsilyl fluoride is proposed.