Furan ring opening–pyrrole ring closure: a new synthetic route to aryl (heteroaryl)-annulated pyrrolo [1, 2-a][1, 4] diazepines

…, VA Shcherbinin, IV Trushkov, DA Cheshkov…

Index: Butin, Alexander V.; Nevolina, Tatyana A.; Shcherbinin, Vitaly A.; Trushkov, Igor V.; Cheshkov, Dmitry A.; Krapivin, Gennady D. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 14 p. 3316 - 3327

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Citation Number: 32

Abstract

A method of synthesis of pyrrolo [1, 2-a][1, 4] benzodiazepines is described. This method is based on the recyclization of N-(furfuryl) anthranilamides under treatment with an aq. HCl/AcOH system and allows one to form both diazepine and pyrrole rings in one step. The reaction proceeds via furan ring opening into a diketone moiety followed by consecutive interaction of the NH2-group with both carbonyl functions. The process is not efficient in ...

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