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Sulfur–Carbon Bond Formation through Ring‐Opening of Triazolothiadiazole with Organometallics
Author(s) -
Othman Raja Ben,
Massip Stéphane,
Marchivie Mathieu,
Jarry Christian,
Vercouillie Johnny,
Chalon Sylvie,
Guillaumet Gérald,
Suzenet Franck,
Routier Sylvain
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.201400151
Subject(s) - chemistry , sulfanyl , ring (chemistry) , alkyl , sulfur , aryl , sequence (biology) , carbon fibers , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , biochemistry , materials science , composite number , composite material
An efficient and convenient method was developed for the formation of S ‐substituted thiotriazoles through an unprecedented organometallic addition and subsequent ring‐opening sequence of 3‐substituted [1,2,4]triazolo[3,4‐ b ][1,3,4]thiadiazole. The method is applicable to a wide range of substrates containing different functional groups and furnishes excellent yields of the corresponding N ‐unsubstituted 3‐ or 5‐alkyl, aryl, alkynyl and alkenyl sulfanyl‐1,2,4‐triazole products.