Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Autor:	Reagan L. Mohlala, Elena Mabel Coyanis, Muhammad Q. Fish, Manuel A. Fernandes, Moira L. Bode
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	multicomponent reaction isocyanides dialkyl acetylenedicarboxylates thiourea α-haloketone thiazine Organic chemistry QD241-441
Zdroj:	Molecules, Vol 26, Iss 18, p 5493 (2021)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules26185493
Popis:	A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.
Databáze:	Directory of Open Access Journals
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