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A MODIFIED BIGINELLI REACTION TOWARD OXYGEN-BRIDGED TETRAHYDROPYRIMIDINES FUSED WITH SUBSTITUTED 1,2,4-TRIAZOLE RING

Mustafa Kemal Gümüş, Nikolay Yu. Gorobets, Yuriy V. Sedash, Valentin A. Chebanov, Sergey M. Desenko
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Abstract


A microwave-assisted Biginelli-like three-component condensation using salicylic aldehyde derivatives, acetone, and 5-substituted 3-amino-1,2,4-triazoles instead of the urea component results in the formation of oxygen-bridged tetrahydrotriazolopyrimidine derivatives (11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocines) in good yields and high purity. A plausible reaction mechanism for this transformation is discussed in details using literature and experimental data.

Keywords


3-amino-1,2,4-triazole; benzoxadiazocine; oxygen-bridged structure; Biginelli reaction; cascade reaction; microwave-assisted synthesis; multicomponent reaction; reaction mechanism

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