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

General Chemistry
General Chemical Engineering

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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 = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = aug,

day = "31",

doi = "10.1021/acsomega.7b00819",

language = "English",

volume = "2",

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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

TY - JOUR

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.

PY - 2017/8/31

Y1 - 2017/8/31

N2 - 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.

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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U2 - 10.1021/acsomega.7b00819

DO - 10.1021/acsomega.7b00819

M3 - Article

AN - SCOPUS:85061271573

SN - 2470-1343

VL - 2

SP - 5137

EP - 5141

JO - ACS Omega

JF - ACS Omega

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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

Abstract

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