Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

Rahul D Shingare; Akshay S Kulkarni; Revannath L Sutar; D Srinivasa Reddy

doi:10.1021/acsomega.7b00819

Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue

ACS Omega. 2017 Aug 31;2(8):5137-5141. doi: 10.1021/acsomega.7b00819. Epub 2017 Aug 29.

Authors

Rahul D Shingare^{1

2}, Akshay S Kulkarni¹, Revannath L Sutar¹, D Srinivasa Reddy^{1

2}

Affiliations

¹ Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
² Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 025, India.

Abstract

A simple and practical method to access a variety of benzimidazol-2-ones is reported here. A series of N-alkyl-substituted benzimidazol-2-ones were synthesized by decarbonylative ring contraction starting from corresponding quinoxalinediones for the first time. The utility of the method has been demonstrated by synthesizing recently approved controversial drug flibanserin (Addyi) and a urea analogue of marine antibiotic natural product hunanamycin-A.