标题: Microwave-Enhanced Efficient Regioselective Synthesis of 1,3,4-Trisubstituted 2-Mercaptoimidazoles on a Soluble Support
作者: Yellol, Gorakh S.
Chou, Cheng-Ting
Chang, Wang-Jin
Maiti, Barnali
Sun, Chung-Ming
应用化学系
Department of Applied Chemistry
关键字: mercaptoimidazoles;microwave chemistry;nitrogen heterocycles;polyethylene glycol;soluble supported synthesis
公开日期: 1-一月-2012
摘要: A novel efficient synthetic method for regioselective synthesis of optically active 2-mercaptoimidazoles with three points of structural diversity was investigated on a polyethylene glycol (PEG) support. The key synthetic steps involve (i) synthesis of thiourea derivatives of polymer-supported amino acids with isothiocyanates and (ii) one-pot regioselective condensation of PEG-linked thiourea with a-bromo ketones to furnish the 2-mercaptoimidazole skeleton under microwave conditions. An excellent regioselectivity was observed during this one-pot condensation reaction which was further supported by NOE studies. In addition to three sets of structural diversity, supplementary chirality at the a-position of the 2-mercaptoimidazole skeleton is the key feature of this synthesis. A representative set of 2-mercaptoimidazoles was efficiently assembled on soluble support utilizing various L-amino acids, isothiocyanates and a-bromoaryl ketones with good yields.
URI: http://dx.doi.org/10.1002/adsc.201100640
http://hdl.handle.net/11536/15285
ISSN: 1615-4150
DOI: 10.1002/adsc.201100640
期刊: ADVANCED SYNTHESIS & CATALYSIS
Volume: 354
Issue: 1
起始页: 187
结束页: 196
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