Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions |
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| Authors: | Reagan L Mohlala Elena Mabel Coyanis Muhammad Q Fish Manuel A Fernandes Moira L Bode |
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| Institution: | 1.Advanced Materials Division, Mintek, Private Bag X3015, Randburg 2125, South Africa; (R.L.M.); (M.Q.F.);2.Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO Wits, Johannesburg 2050, South Africa; |
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| Abstract: | 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%. |
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| Keywords: | multicomponent reaction isocyanides dialkyl acetylenedicarboxylates thiourea α -haloketone thiazine thiazole-pyrimidines |
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