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DOI: 10.1055/a-2260-0420
Synthesis of Alkyl Thiochromano[2,3-c]pyrrole-9-carboxylate Derivatives Utilizing Benzo[b]thiofuran-2,3-dione, Maleimides, and Alkyl Alcohol/Water Mixtures
We wish to thank the Deanship of Scientific Research, University of Jordan (project no 41/2022) and the University of Petra (project no 9/4/2022) for financial support.
Dedicated with best wishes to Professor Adel A. Jarar on the occasion of his 92nd birthday
Abstract
A set of thiochromano[2,3-c]pyrrolidine-1,3-diones, incorporating α-hydroxy esters and their acids at the C-9 position, was prepared via direct interaction involving benzo[b]thiofuran-2,3-diones, maleimides, and alkyl alcohols in water at 90 °C. Structures of the new products were deduced from HRMS and NMR spectral data and confirmed by single-crystal X-ray crystallography. An insight into a proposed pathway involving a sequential Michael conjugate addition (initiated by the sulfur atom) and an aldol-type reaction is presented.
Key words
benzo[b]thiofuran-2,3-dione - N-substituted maleimides - domino Michael–aldol reactions - thiochromano[2,3-c]pyrrolidines - ring expansionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2260-0420.
- Supporting Information
Publication History
Received: 22 December 2023
Accepted after revision: 02 February 2024
Accepted Manuscript online:
02 February 2024
Article published online:
22 February 2024
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