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

Rahul D. Shingare, Akshay S. Kulkarni, Revannath L. Sutar, D. Srinivasa Reddy

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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.

Original language	English
Pages (from-to)	5137-5141
Number of pages	5
Journal	ACS Omega
Volume	2
Issue number	8
DOIs	https://doi.org/10.1021/acsomega.7b00819
State	Published - 31 Aug 2017
Externally published	Yes

ASJC Scopus subject areas

Chemistry (all)
Chemical Engineering (all)

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Shingare, R. D., Kulkarni, A. S., Sutar, R. L., & Srinivasa Reddy, D. (2017). 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, 2(8), 5137-5141. https://doi.org/10.1021/acsomega.7b00819

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title = "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",

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.",

author = "Shingare, {Rahul D.} and Kulkarni, {Akshay S.} and Sutar, {Revannath L.} and {Srinivasa Reddy}, D.",

note = "Funding Information: We thank the CSIR (ORIGIN: CSC0108 and NICE-P: CSC0109 programs under XII Five Year Plan) for the financial support. R.D.S. thanks UGC for the award of a research fellowship. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = aug,

day = "31",

doi = "10.1021/acsomega.7b00819",

language = "English",

volume = "2",

pages = "5137--5141",

journal = "ACS Omega",

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Shingare, RD, Kulkarni, AS, Sutar, RL & Srinivasa Reddy, D 2017, '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, vol. 2, no. 8, pp. 5137-5141. https://doi.org/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. / Shingare, Rahul D.; Kulkarni, Akshay S.; Sutar, Revannath L. et al.

In: ACS Omega, Vol. 2, No. 8, 31.08.2017, p. 5137-5141.

Research output: Contribution to journal › Article › peer-review

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T1 - Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones

T2 - Application to the synthesis of flibanserin, a drug for treating hypoactive sexual desire disorder in women and marine natural product hunanamycin analogue

AU - Shingare, Rahul D.

AU - Kulkarni, Akshay S.

AU - Sutar, Revannath L.

AU - Srinivasa Reddy, D.

N1 - Funding Information: We thank the CSIR (ORIGIN: CSC0108 and NICE-P: CSC0109 programs under XII Five Year Plan) for the financial support. R.D.S. thanks UGC for the award of a research fellowship. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/8/31

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AB - 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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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

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