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Domino Condensation/S‐Arylation/Heterocyclization Reactions: Copper‐Catalyzed Three‐Component Synthesis of 2‐N‐Substituted Benzothiazoles
Author(s) -
Ma Dawei,
Lu Xu,
Shi Liu,
Zhang Hui,
Jiang Yongwen,
Liu Xiangqian
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201005787
Subject(s) - domino , chemistry , carbon disulfide , substituent , aryl , alkyl , combinatorial chemistry , catalysis , nucleophile , condensation , organic chemistry , physics , thermodynamics
All in it together : A highly efficient and extremely versatile method for the assembly of benzothiazoles with a nitrogen substituent in the 2‐position relies on a copper‐catalyzed cascade reaction of a 2‐haloaniline, carbon disulfide, and an N nucleophile (see scheme). The products are useful precursors for the synthesis of a range of important pharmaceutical agents. DMF= N , N ‐dimethylformamide; R,R′=H, alkyl, aryl; Z=Me, CF 3 , CO 2 Me, CN, N 2 O, Cl, F, Ac.