Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Substituent-Controllable Cascade Regioselective Annulation of β-Enaminones with N-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles

Version 1 : Received: 13 May 2023 / Approved: 15 May 2023 / Online: 15 May 2023 (07:16:26 CEST)

A peer-reviewed article of this Preprint also exists.

Wang, H.; Zhou, T.; Wu, M.; Ye, Q.; He, X. Substituent-Controllable Cascade Regioselective Annulation of β-Enaminones with N-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles. Molecules 2023, 28, 4416. Wang, H.; Zhou, T.; Wu, M.; Ye, Q.; He, X. Substituent-Controllable Cascade Regioselective Annulation of β-Enaminones with N-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles. Molecules 2023, 28, 4416.

Abstract

A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of N-sulfonyl-1,2,3-trizaoles with β-enaminones. The imidazole ring was formed through 1,1-insertion of N-H bond to α-imino rhodium carbene and subsequential intramolecular 1,4-conjugate addition when α-carbon atom of amino group bearing with methyl, whereas utilizing phenyl substituent constructed pyrrole ring via intramolecular nucleophilic addition. Features such as mild conditions, good functional groups tolerance, gram-scale synthesis, and valuable transformations of the products qualified this unique protocol as an efficient tool for the synthesis of N-heterocycles.

Keywords

annulation; β-enaminones; imidazoles; pyrroles; N-sulfonyl trizaoles

Subject

Chemistry and Materials Science, Organic Chemistry

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