Copper(I)-Catalyzed Formal [4 + 2] Cyclocondensation of -Hydroxybenzyl Alcohol, Aromatic Terminal Alkynes, and Sulfonyl Azides: An Alternative Approach to 2-Sulfonyliminocoumarins.

Molecules

Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.

Published: July 2024

In this paper, an alternative and efficient copper(I)-catalyzed synthesis of 2-sulfonyliminocoumarins is developed through a three-component reaction of -hydroxybenzyl alcohol, alkynes, and -toluenesulfonyl azide. The proposed route for access to the 2-iminocoumarin ring involves a [4 + 2] hetero-Diels-Alder reaction between -quinone methide and ketenimine intermediates generated in situ.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11279675PMC
http://dx.doi.org/10.3390/molecules29143426DOI Listing

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