邻硝基苯胺还原关环一步法合成苯并咪唑类化合物

上海大学学报(自然科学版) ›› 2007, Vol. 13 ›› Issue (1): 77-81 .

邻硝基苯胺还原关环一步法合成苯并咪唑类化合物

朱洪;黄文忠;浦家齐

上海大学理学院，上海 200444

收稿日期:2006-05-16 出版日期:2007-02-28 发布日期:2007-02-28

Synthesis of Benzimidazoles from o Nitroanilines in a One Step Reductive Cyclization Process

ZHU Hong;HUANG Wen zhong;PU Jia qi

School of Sciences, Shanghai University, Shanghai 200444, China

Received:2006-05-16 Online:2007-02-28 Published:2007-02-28

摘要/Abstract

摘要： 邻硝基苯胺( 1〖STBZ〗, 4〖STBZ〗)与芳香醛( 2〖STBZ〗〖WTHZ 〗a 〖WTHZ〗c )在连二亚硫酸钠存在下共热，发生还原关环反应，一步即可合成苯并咪唑类化合物( 3〖STBZ〗〖WTHZ〗a 〖WTHZ〗c〖WTBZ 〗, 5〖STBZ〗〖WTHZ〗a 〖WTHZ〗c ).当起始物中含有不止一个硝基时，连二亚硫酸钠对硝基的还原有选择性.反应以乙醇水为溶剂，水可加速反应进程.

关键词: 苯并咪唑, 环化反应, 连二亚硫酸钠, 硝基化合物, 选择性还原

Abstract: Benzimidazoles ( 3a 〖WTHZ〗c〖WTBZ 〗, 5〖STBZ〗〖WTHZ〗a 〖WTHZ〗c ) were synthesized in a one step reductive c yclization reaction of o nitroanilines ( 1〖STBZ〗, 4〖STBZ 〗) and aryl aldehydes ( 2〖STBZ〗〖WTHZ〗a 〖WTHZ〗c ). Sodium dithionite was used as a reductive reagent. Selectivity was found when more than one nitro group existed in the substrates. A mixture of ethanol and water was u sed as solvent. The reaction was accelerated by water.

Key words: cyclization, nitro compound, selective reduction , sodium dithionite, benzimidazole

朱洪;黄文忠;浦家齐. 邻硝基苯胺还原关环一步法合成苯并咪唑类化合物[J]. 上海大学学报(自然科学版), 2007, 13(1): 77-81 .

ZHU Hong;HUANG Wen zhong;PU Jia qi . Synthesis of Benzimidazoles from o Nitroanilines in a One Step Reductive Cyclization Process[J]. Journal of Shanghai University（Natural Science Edition）, 2007, 13(1): 77-81 .