Metal-Free Synthesis of 2‑Aminobenzothiazoles via Aerobic Oxidative Cyclization/Dehydrogenation of Cyclohexanones and Thioureas

A metal-free process for the synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas has been developed using catalytic iodine and molecular oxygen as the oxidant under mild conditions. Various 2-aminobenzothiazoles, 2-aminonaphtho[2,1-d]thiazoles, and 2-aminonaphtho[1,2-d]thiazoles wer...

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Published inOrganic letters Vol. 15; no. 11; pp. 2604 - 2607
Main Authors Zhao, Jinwu, Huang, Huawen, Wu, Wanqing, Chen, Huoji, Jiang, Huanfeng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2013
Amer Chemical Soc
Subjects
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Cyclohexanones - chemistry
Iodine - chemistry
Metals
Molecular Structure
Oxidation-Reduction
Oxygen - chemistry
Physical Sciences
Science & Technology
Thiazoles - chemistry
Thiourea - chemistry
RILUZOLE
R116010
S BOND FORMATION
ONE-POT SYNTHESIS
CATALYZED OXIDATION
CONVERSION
BENZOXAZOLES
2-SUBSTITUTED BENZOTHIAZOLES
CYCLIZATION
MOLECULAR-OXYGEN
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Summary:A metal-free process for the synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas has been developed using catalytic iodine and molecular oxygen as the oxidant under mild conditions. Various 2-aminobenzothiazoles, 2-aminonaphtho[2,1-d]thiazoles, and 2-aminonaphtho[1,2-d]thiazoles were prepared via this method in satisfactory yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400773k