Facile Preparation of Indoles and 1,2‐Benzothiazine 1,1‐Dioxides: Nucleophilic Addition of Sulfonamides to Bromoacetylenes and Subsequent Palladium‐Catalyzed Cyclization | Zendy

Yamagishi Masahito | Zendy; Nishigai Ken | Zendy; Ishii Azusa | Zendy; Hata Takeshi | Zendy; Urabe Hirokazu | Zendy

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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).

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