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CONVENIENT SYNTHETIC PATH TO ETHYL 1-ARYL-5-FORMYL-1H-1,2,3-TRIAZOLE-4-CARBOXYLATES AND 1-ARYL-1,5-DIHYDRO-4H-[1,2,3]TRIAZOLO[4,5-d]PYRIDAZIN-4-ONES

Nazariy Pokhodylo, Olga Shyyka, Mykola Obushak
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Abstract


A convenient method for selective synthesis of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones has been developed. New ethyl 1-aryl-5-(diethoxymethyl)-1H-1,2,3-triazole-4-carboxylates were prepared by the reaction of different aryl azides and ethyl 4,4-diethoxy-3-oxobutanoate and readily converted into ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates in high overall yields. Such aldehydes were found to be reactive in several condensation reactions. Reaction of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and hydrazine provided 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones in excellent yields.

 


Keywords


aryl azide; ethyl 4,4-diethoxy-3-oxobutanoate; 1H-1,2,3-triazole; [1,2,3]triazolo[4,5-d]pyridazine; base-promoted cyclocondensation

Full Text: PDF Supplementary File(s): Single-crystal X-ray diffraction data (486KB)


 

 

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