The highly efficient cycloaddition reaction of hydrazonyl chlorides with 2,3-dichloro-1,4-naphthoquinone yielded pharmaceutically important spiro-naphthalene-1,2'-[1,3,4]oxadiazol-4-ones with moderate to good yields under batch and flow synthesis methods. The obtained products were elucidated by IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction technique (only for 6h). The synthesized molecules have been subjected to theoretical analysis by quantum chemical calculations at B3LYP/6-31G(d,p) level, which provided supporting data for the experimental findings.
Keywords: naphthoquinones; flow chemistry; batch chemistry; cycloaddition reaction; spiran 1,3,4-oxadiazole, DFT, and X-ray diffraction.
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Saleh, L. Y.; Altıntaş, B.; Filiciotto, L.; Zorlu, Y.; Luque, R.; Altug, C. Beilstein Arch. 2021, 202189. doi:10.3762/bxiv.2021.89.v1
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