Background: Nitrosocarbonyl intermediates are fleeting compounds obtainable from the periodate
oxidation of hydroxamic acids and easily trapped with dienes and alkenes to give the products of
hetero Diels-Alder and ene reactions in high yields.
Methods: A fleeting heterocyclic nitrosocarbonyl derived from the corresponding nitrile oxide is at work
in a short-cut synthesis of 4-bromo-N-[(1R*,4S*)-4-hydroxy-2-cyclohexen-1-yl]-2-thiazolecarboxamide.
The synthetic strategy is based on hetero Diels-Alder cycloaddition followed by mild reductive cleavage
of the N-O bond.
Results: A new 2-thiazolecarboxamide derivative is obtained in good yields and the results of the invitro
antiviral tests are briefly discussed. The product was found active against HPV virus and some
structural evidences allow shining some light on future perspectives on the application of pericyclic reactions
to the synthesis of biological active molecules.
Conclusion: The findings demonstrated that the synthetic methodology works well for the preparation
of heterocyclic substituted novel compounds that displayed interesting and promising activity against
viruses and in particular against the HPV.
Keywords: Antiviral tests, bioisostere structures, human papilloma virus inhibitors, nitrile oxides, nitrosocarbonyls, nucleoside
analogues, thiazole derivatives.
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