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Abstract
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9-(Aryl)thiazolo [4,5-d] [1,2,4]triazolo [1,5-a]pyrimidin-2(3H)-ones have been efficaciously synthesized in good yields via reaction of aldehydes, 2,4-thiazolidinedione and 3-amino-1,2,4-triazole under the solvent- free condition at 100 °C by using a catalytic amount (1 mg) of Fe 3 O 4 @SiO 2 @Methotrexate. This reaction proceeded via a cooperative anomeric based oxidation (ABO) pathway. The reaction condition is appro- priate due to the easy experimental procedure and product separation. It is a three-component reaction that lets the building of rather complex sulfur including heterocyclic categories by using simple reactants. The competition of reaction mechanisms (both thermodynamically and kinetically) for the formation of 9-phenylthiazolo [4,5-d] [1,2,4]triazolo [1,5- α]pyrimidin-2(3H)-one and 5-phenylthiazolo [5,4-e] [1,2,4]tri- azolo [1,5- α]pyrimidin-7(8H)-one is also computationally compared at M06/def2-SVP. The synthesized Fe 3 O 4 @SiO 2 @Methotrexate MNPs catalyst was characterized by several techniques such as FT–IR, EDX, WDX, XRD, FE-SEM, TEM, TGA, DTA, and VSM analyses. The catalyst was recycled and reused in six next runs without any important activity.
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