Tandem Reactions of Thermolysis and [3+2] Cycloaddition in the Synthesis of 3-Hetaryl-4-Nitrofuroxans from 4-Nitrofuroxannitrolic Acid

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 sy...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-05, Vol.56 (5), p.607-610
Main Authors: Larin, Alexander А., Fershtat, Leonid L., Makhova, Nina N.
Format: Article
Language:English
Subjects:
Alkenes
Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Cycloaddition
Heterocyclic compounds
Nitric oxide
Organic Chemistry
Pharmacy
Pyrolysis
Stereoselectivity
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02706-4