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Glyoxylic acid in the reaction of isatoic anhydride with amines: a rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones leading to rutaecarpine and evodiamine |
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| Authors: | K Raghavendra Rao Akula Raghunadh Ramamohan Mekala Suresh Babu Meruva TV Pratap T Krishna Dipak Kalita Eppakayala Laxminarayana Bagineni Prasad Manojit Pal |
| Institution: | 1. Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Limited, Bollaram Road Miyapur, Hyderabad 500 049, India;2. Sreenidhi Institute of Science and Technology (Autonomous), Yamnampet, Ghatkesar, Hyderabad 501 301, India;3. Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India |
| Abstract: | A dual reactant/catalyst role of glyoxylic acid in the reaction of isatoic anhydride with various amines afforded a novel, robust and rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones. This metal catalyst-free reaction proceeds via an unusual and unexpected cleavage of C–C bond. A shorter and common route to two alkaloids, that is, rutaecarpine and evodiamine is also accomplished. |
| Keywords: | Glyoxylic acid Isatoic anhydride Amine Rutaecarpine Evodiamine |
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