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TANDEM REACTIONS OF THERMOLYSIS AND [3+2] CYCLOADDITION IN THE SYNTHESIS OF 3-HETARYL-4-NITROFUROXANS FROM 4-NITROFUROXANNITROLIC ACID

Александр А. Ларин, Леонид Л. Ферштат, Нина Н. Махова
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Abstract


A tandem method of synthesis of 3-hetaryl-4-nitrofuroxans was developed based on the one-pot sequence of thermolysis of 4-nitrofuroxannitrolic acid to the corresponding 4-nitro-3-furoxancarbonitrile oxide and [3+2] cycloaddition of the latter to acetylenes and olefins. It was established that the synthesized 3-(isoxazol-3-yl)- and 3-(isoxazolin-3-yl)-4-nitrofuroxans are formed with high regioand diastereoselectivity.

Keywords


nitrofuroxans; nitrolic acids; 1,2,5-oxadiazoles; cycloaddition; regioselectivity.

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