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Facile Preparation of Indoles and 1,2‐Benzothiazine 1,1‐Dioxides: Nucleophilic Addition of Sulfonamides to Bromoacetylenes and Subsequent Palladium‐Catalyzed Cyclization
Author(s) -
Yamagishi Masahito,
Nishigai Ken,
Ishii Azusa,
Hata Takeshi,
Urabe Hirokazu
Publication year - 2012
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.201201024
Subject(s) - benzothiazine , palladium , bromine , chemistry , nucleophile , catalysis , nitrogen atom , medicinal chemistry , nucleophilic addition , nitrogen , organic chemistry , group (periodic table)
Bromine as a double agent : The bromine atom in 1‐bromo‐1‐alkynes works as an electron‐withdrawing group to effect the nucleophilic addition of sulfonamides. It again plays a pivotal role in the palladium‐catalyzed cyclization of the resultant ( Z )‐2‐(sulfonylamino)‐1‐bromoalkenes into nitrogen heterocycles (see scheme).