Premium
Synthesis of 3‐Amino‐1‐benzothiophene‐1,1‐diones by Alkyne Directed Hydroarylation and 1/N→3/C‐Sulfonyl Migration
Author(s) -
Bernar Ivan,
BlancoAnia Daniel,
Stok Sophie J.,
Sotorríos Lia,
GómezBengoa Enrique,
Rutjes Floris P. J. T.
Publication year - 2018
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.201801062
Subject(s) - benzothiophene , chemistry , alkyne , regioselectivity , intramolecular force , sulfonyl , stereoselectivity , medicinal chemistry , triple bond , stereochemistry , catalysis , organic chemistry , double bond , thiophene , alkyl
A completely regioselective and highly stereoselective palladium‐catalyzed intramolecular hydroarylation of arenesulfonyl ynamines to benzothiazoles was developed. The presence of an electron‐withdrawing group on the triple bond of the sulfonyl ynamine was crucial for the success of the reaction and our mechanistic studies suggest an alkyne‐directed 5‐ exo ‐dig cyclization pathway. The products easily underwent photoinduced rearrangement to 3‐amino‐1‐benzothiophene‐1,1‐diones (up to 35 % yields after two steps).