Preparation of Benzothiazoles and Heterocyclic Spiro Compounds Through Cu-catalyzed S-S Bond Cleavage and C-S Bond Formation

The reaction of 2,2'-dithiobis(benzenamine)s with various aldehydes in the presence of CuOAc catalyst under air without any additives afforded the corresponding benzothiazoles. When cycloalkylcarbaldehydes were reacted under similar conditions, benzothiazoles and heterocyclic spiro compounds we...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 11; no. 9
Main Authors Minami, Keisuke, Minakawa, Maki, Uozumi, Yasuhiro
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.09.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACIDS
ADME
S-S bond cleavage
benzothiazole
C-S bond formation
CONVENIENT
DISULFIDES
ELEMENTAL SULFUR
REDUCTION
heterocyclic spiro compound
BIOLOGICAL EVALUATION
CuOAc
CHEMOTYPES DESIGN
DERIVATIVES
CYCLIZATION
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Summary:The reaction of 2,2'-dithiobis(benzenamine)s with various aldehydes in the presence of CuOAc catalyst under air without any additives afforded the corresponding benzothiazoles. When cycloalkylcarbaldehydes were reacted under similar conditions, benzothiazoles and heterocyclic spiro compounds were produced. Gram-scale preparation was successfully performed in the presence of CuOAc catalyst under open-flask conditions.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200211