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Synthesis of Benzothiazoles through Copper‐Catalyzed One‐Pot Three‐Component Reactions with Use of Sodium Hydrosulfide as a Sulfur Surrogate
Author(s) -
Park Namjin,
Heo Yumi,
Kumar Manian Rajesh,
Kim Yong,
Song Kwang Ho,
Lee Sunwoo
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.201101773
Subject(s) - chemistry , benzothiazole , catalysis , sodium iodide , copper , aryl , sulfur , organic chemistry , aldehyde , medicinal chemistry , iodine , alkyl
Copper‐catalyzed one‐pot three‐component reactions of 2‐iodoanilines, aldehydes, and NaSH · n H 2 O afford benzothiazoles in good yields. When CuCl was employed as a catalyst in the absence of a ligand, a variety of aromatic aldehydes and substituted 2‐iodoanilines reacted with NaSH · n H 2 O to produce the corresponding 2‐arylbenzothiazoles in 70–98 % yields. The copper catalyst plays a key role in C–S bond formation between NaSH · n H 2 O and the aryl iodide that was formed from the condensation of 2‐iodoaniline and aldehyde. It was found that NaSH · n H 2 O functions as a sulfur surrogate and oxidant in the formation of benzothiazole.