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Synthesis of nitro and amino N-heterocycles via ring transformation of 2-methyl-3-nitrochromone
Abstract
2-Methyl-3-nitrochromone (1) reacted with acid hydrazides, S-methylisothiourea, hydroxylamine and ethyl aminoethanoate to give the nitro derivatives of pyrazole 2, pyrimidine 6, isoxazole 11 and pyrrole 13, respectively. These nitro compounds were reduced by catalytic hydrogenation to the corresponding amino derivatives. In the case of 2, a rearrangement of the acyl group took place during the reduction. Substitution reactions of the 2-methylthio group in 6 were also described.
