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 | Zendy

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

Open Access

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

Author(s) -

Rahul D. Shingare,

Akshay S. Kulkarni,

Revannath L. Sutar,

D. Srinivasa Reddy

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00819

Subject(s) - natural product , drug , ring (chemistry) , chemistry , sildenafil , stereochemistry , combinatorial chemistry , pharmacology , medicine , organic chemistry

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.

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