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Mannich‐Type Addition Reactions between Lithium Derivatives of Benzo[ d ]thiazoles and N ‐ tert ‐Butylsulfinyl‐3,3,3‐trifluoroacetaldimine: Convenient Generalized Synthesis of Bis(benzothiazole)s
Author(s) -
Mei Haibo,
Dai Yanling,
Wu Lingmin,
Soloshonok Vadim A.,
Han Jianlin,
Pan Yi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400118
Subject(s) - chemistry , benzothiazole , lithium (medication) , combinatorial chemistry , scope (computer science) , mannich reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , endocrinology , computer science , programming language
This study describes the anomalous outcome of the Mannich‐type reaction of N ‐ tert ‐butylsulfinyl‐3,3,3‐trifluoroacetaldimine and Li derivatives of benzo[ d ]thiazoles, which offers a convenient and generalized method for the synthesis of biologically relevant ( E )‐1,2‐bis(2‐benzothiazolyl)ethanes. The mechanism, scope, and scalability of this new reaction are discussed.