Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage
2024; American Chemical Society; Volume: 89; Issue: 4 Linguagem: Inglês
10.1021/acs.joc.3c02539
ISSN1520-6904
AutoresPeng Zhao, You Zhou, Can Wang, An‐Xin Wu,
Tópico(s)Synthesis of heterocyclic compounds
ResumoA 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 C═C bonds in enaminones involves a bicyclization/ring-opening and oxidative coupling sequence.
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