Shaik Siddiq Pasha, Sultana Faria, Ravikumar A, Sunkari Satish, Alarifi Abdullah, Kamal Ahmed
Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad-500007, India.
Org Biomol Chem. 2017 Sep 20;15(36):7696-7704. doi: 10.1039/c7ob01778b.
A novel I promoted, highly efficient metal-free and peroxide-free greener domino protocol for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes has been developed via oxidative cleavage of the C(sp)-H bond, followed by C3-nucleophilic attack of IBT and oxidation. Interestingly, under these conditions 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)aniline gave the benzo[4',5']thiazolo[2',3':2,3]imidazo[4,5-c]quinoline derivative via oxidative cleavage of the C(sp)-H bond, followed by Pictet-Spengler cyclization and aromatization. This method offers the advantages of broad substrate scope, ecofriendly feature and high atom economy apart from higher yields.
我所推动的一项新研究，通过C(sp)-H键的氧化裂解，随后进行苯并[d]咪唑并[2,1-b]噻唑（IBTs）与苯乙烯的C3-二羰基化反应，开发出了一种高效、无金属且无过氧化物的更绿色多米诺反应方案，接着是IBT的C3-亲核进攻和氧化。有趣的是，在这些条件下，2-(苯并[d]咪唑并[2,1-b]噻唑-2-基)苯胺通过C(sp)-H键的氧化裂解，随后进行Pictet-Spengler环化和芳构化反应，生成了苯并[4',5']噻唑并[2',3':2,3]咪唑并[4,5-c]喹啉衍生物。除了产率更高外，该方法还具有底物范围广、环境友好和原子经济性高的优点。
