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Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent |
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| Authors: | Alicia Foucourt Elizabeth Chosson Catherine Buquet Bertrand Leblond Thierry Besson |
| Affiliation: | a Université de Rouen, CNRS UMR 6014—C.O.B.R.A. & FR3038, I.R.C.O.F. rue Tesnière, F-76130 Mont Saint-Aignan, France b Université de Rouen, EA 3829, UFR Médecine-Pharmacie, 22 Boulevard Gambetta, 76183 Rouen cedex 1, France c Milestone S.r.l., Via Fatebenefratelli, 1/5, 24010 Sorisole (BG), Italy d ExonHit Therapeutics, 65 Boulevard Masséna, F-75013, Paris, France e INSA de Rouen, CNRS UMR 6014—C.O.B.R.A. & FR3038, I.R.C.O.F. rue Tesnière, F-76130 Mont Saint-Aignan, France |
| Abstract: | A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to Azixa™ (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. |
| Keywords: | 4-Anilinoquinazolines Microwave-assisted synthesis Dimroth rearrangement |
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