Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via CâC Bond Cleavage.
J Org Chem
; 89(4): 2505-2515, 2024 Feb 16.
Article
en En
| MEDLINE
| ID: mdl-38315825
ABSTRACT
A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means of synthesizing a variety of fully substituted thiazoles by constructing C-C(CO), C-S, and C-N bonds. This transformation allows the realization of enaminones as unusual aryl C2 synthons and simultaneously allows the thioylation and dicarbonylation of α-C sites. A preliminary mechanistic study was performed and indicated that the cleavage of CâC bonds in enaminones involves a bicyclization/ring-opening and oxidative coupling sequence.
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2024
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Article