Synthesis of Benzoxazoles by an Efficient Ullmann-Type Intramolecular C(aryl)-O Bond-Forming Coupling Cyclization with a BINAM-Copper(II) Catalyst

被引：36
作者：
Naidu, Ajay B. [1 ]
Sekar, Govindasamy [1 ]
机构：
[1] Indian Inst Technol Madras, Dept Chem, Madras 600036, Tamil Nadu, India
来源：
SYNTHESIS-STUTTGART | 2010年 / 04期
关键词：
copper catalyst; nitrogen ligands; C-O bond formation; Ullmann coupling; benzoxazole synthesis; REVERSE-TRANSCRIPTASE INHIBITORS; BUTYL HYDROPEROXIDE; PARALLEL SYNTHESIS; CARBOXYLIC-ACIDS; CARBONYL OXYGEN; MILD CONDITIONS; O-ARYLATION; DERIVATIVES; OXIDATION; DESIGN;
D O I：
10.1055/s-0029-1218589
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A wide range of 2-substituted benzoxazoles were synthesized from the corresponding N-(2-iodophenyl) benzamides through intramolecular C-(aryl)-O bond formation via Ullmann-type coupling cyclization in the presence of a catalytic amount of an easily available BINAM-copper(II) complex under very mild reaction conditions (82 degrees C). Less reactive bromo and chloro analogues of the N-(2-halophenyl) benzamides were also successfully cyclized to produce benzoxazoles, without increasing the catalyst loading.
引用
收藏
页码：579 / 586
页数：8
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