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Hypervalent Iodine Mediated Intramolecular Cyclization of Thioformanilides: Expeditious Approach to 2-Substituted Benzothiazoles

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D. Subhas Bose* and Mohd. Idrees

Organic Chemistry Division III, Fine Chemicals Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India dsb@iict.res.in; bose_iict@yahoo.co.in

J. Org. Chem., 2006, 71 (21), pp 8261–8263

DOI: 10.1021/jo0609374

Publication Date (Web): September 15, 2006

To whom correspondence should be addressed. Fax: +91-40-27160387.

Abstract

A new, mild, and efficient method has been developed for the synthesis of 2-substituted benzothiazoles via the intramolecular cyclization of thioformanilides by using hypervalent iodine reagents in CH₂Cl₂ at ambient temperature. The reaction proceeds via a thiyl radical in high yields to give the novel compound oxybis benzothiazole and is also amenable to generating combinatorial libraries of heterocyclic compounds by solid-phase synthesis.

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Published In Issue October 13, 2006
Received May 5, 2006

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Hypervalent Iodine Mediated Intramolecular Cyclization of Thioformanilides: Expeditious Approach to 2-Substituted Benzothiazoles

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides

Metal-Free Cascade Intramolecular S-Arylation: Regioselective Synthesis of Substituted Benzothiazoles

An Efficient, PIFA Mediated Approach to Benzo-, Naphtho-, and Heterocycle-Fused Pyrrolo[2,1-c][1,4]diazepines. An Advantageous Access to the Antitumor Antibiotic DC-81

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