Synthesis of Some Novel 2,3,4,8,9‐Pentahydro‐7‐(4‐haloaryl)‐pyrazolo[5,1‐e]benzo[1,5]oxazocines and 2,3(erythro), 7,8‐Tetrahydro‐2‐aryl‐3‐(4‐fluoro‐3‐methylbenzoyl)‐6‐(4‐haloaryl)pyrazolo[5,1‐d] Benzo[1,4]oxazepines via Solid–Liquid PTC

Abstract

In this communication, a simple and straightforward procedure for the heterocyclization of 1H‐4,5‐dihydro‐3‐(4‐haloaryl)‐5‐substituted phenylpyrazoles (4) with 1‐bromo‐3‐chloropropane and 2,3‐dibromo‐1‐(4‐fluoro‐3‐methylphenyl)‐3‐phe‐ nylpropanone affording 2,3,4,8,9‐pentahydro‐7‐(4‐haloaryl)pyrazolo[5,1‐e]benzo[1,5] oxazocines 5 and regioselective synthesis of 2,3(erythro),7,8‐tetrahydro‐2‐ aryl‐3‐(4‐fluoro‐3‐methylbenzoyl)‐6‐(4‐halophenyl)pyrazolo[5,1‐d]benzo[1,4]oxa‐ zepines 6, respectively, via solid–liquid PTC is reported. All the synthesized compounds have been characterized on the basis of their spectral studies (IR, PMR, and MS) and analytical data.

Keywords:

• 1,4‐benzoxazepines
• 1,5‐benzoxazocines
• dihaloalkane
• heterocyclization
• pyrazoles
• regioselective synthesis
• solid–liquid phase‐transfer catalysis

Acknowledgments

Authors are thankful to University Grants Commission (UGC), New Delhi, for financial assistance. Authors also record their sincere thanks to V. J. Ram, emeritus scientist, Medicinal Chemistry Division, Central Drug Research Institute (CDRI), Lucknow, and K. P. Madhusudanan, deputy director and head, sophisticated analytical instrument facility (SAIF), CDRI, Lucknow, for spectral and analytical analyses.