Convenient Synthesis of Benzothiazoles and Benzimidazoles through Brønsted Acid Catalyzed Cyclization of 2‑Amino Thiophenols/Anilines with β‑Diketones

Brønsted acid catalyzed cyclization reactions of 2-amino thiophenols/anilines with β-diketones under oxidant-, metal-, and radiation-free conditions are described. Various 2-substituted benzothiazoles/benzimidazoles are obtained in satisfactory to excellent yields. Different groups such as methyl, c...

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Published inOrganic letters Vol. 16; no. 3; pp. 764 - 767
Main Authors Mayo, Muhammad Shareef, Yu, Xiaoqiang, Zhou, Xiaoyu, Feng, Xiujuan, Yamamoto, Yoshinori, Bao, Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2014
Amer Chemical Soc
Subjects
Aniline Compounds - chemistry
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Ketones - chemistry
Molecular Structure
Phenols - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfhydryl Compounds - chemistry
1,3-DIALKYNES
BENZAZOLES
ONE-POT SYNTHESIS
BENZOXAZOLES
CONDENSATION
MICROWAVE IRRADIATION
EFFICIENT
DERIVATIVES
COPE-TYPE HYDROAMINATION
2-SUBSTITUTED BENZIMIDAZOLES
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Summary:Brønsted acid catalyzed cyclization reactions of 2-amino thiophenols/anilines with β-diketones under oxidant-, metal-, and radiation-free conditions are described. Various 2-substituted benzothiazoles/benzimidazoles are obtained in satisfactory to excellent yields. Different groups such as methyl, chloro, nitro, and methoxy linked on benzene rings were tolerated under the optimized reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403475v