Alternative approach to access 5‑hydroxy-1H-pyrrol-2-(5H)-ones from base-induced tandem intramolecular cyclization of sulfur ylide with ketones and 1,3-hydroxy rearrangement

Preetham,, Habbanakuppe D. and Sharath Kumar,, Kothanahally S. and Aravind,, Kandaswamy and Shobith,, Rangappa and Gatasheh,, Mansour K. (2023) Alternative approach to access 5‑hydroxy-1H-pyrrol-2-(5H)-ones from base-induced tandem intramolecular cyclization of sulfur ylide with ketones and 1,3-hydroxy rearrangement. ACS Publications, 8 (50). pp. 48251-48257. ISSN 24701343

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Abstract

An easily adaptable protocol for the preparation of 5-hydroxy-1H-pyrrol-2(5H)-ones from readily available starting materials has been reported. The reaction of sulfur ylides with carbonyl compounds is a common approach to synthesizing epoxides. Alternatively, we have developed a method with mild reaction conditions wherein sulfur ylide underwent an intramolecular cyclization with a ketonic carbonyl group in a highly efficient way and was followed by 1,3-hydroxy rearrangement to produce 5- hydroxy-1H-pyrrol-2(5H)-ones in excellent yields. The present method offers a straightforward approach to synthesize 5-hydroxy1H-pyrrol-2(5H)-ones from sulfur ylides without the aid of transition metal in one-pot operation, which involves sequential cyclization and rearrangement reaction. The formation of 5-hydroxy-1H-pyrrol-2(5H)-ones is supported by different spectroscopic techniques, including X-ray crystallographic data and 2D NMR studies (COSY, HSQC, HMBC, and DEPT).

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Mr Umendra uom
Date Deposited:	25 Nov 2025 09:37
Last Modified:	25 Nov 2025 09:37
URI:	http://eprints.uni-mysore.ac.in/id/eprint/18049

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