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Copper‐Mediated One‐Pot Access to Benzo[ b ][1,4]thiazines from 2‐ N ‐Sulfonylaminoaryl Disulfides
Author(s) -
Viglianisi Caterina,
Bonaccorsi Paola,
Simone Lavinia,
Nassini Lucia,
Menichetti Stefano
Publication year - 2012
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.201200023
Subject(s) - chemistry , thiazine , salt (chemistry) , copper , alkene , base (topology) , redox , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
2‐ N ‐Sulfonylaminoaryl disulfides can be converted into the corresponding benzo[ b ][1,4]thiazines in one pot when reacted with an electron‐rich alkene in the presence of a base and a substoichiometric amount of a copper salt. Depending upon the reaction conditions, and in particular the copper salt used, we observed the concurrent formation of variable amounts of the corresponding benzo[ b ][1,4]thiazine S ‐oxides that are not the result of a post‐oxidation reaction. The overall procedure can provide simple access to benzo[ b ]thiazines or thiazine S , S ‐dioxides by sequential reduction or oxidation of the crude reaction mixtures.