Elsevier

Tetrahedron

Volume 23, Issue 11, 1967, Pages 4317-4321
Tetrahedron

The reactions of flavanone with substituted hydrazines

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Abstract

The reactions of flavanone with seven substituted hydrazines (H2N-NHR; R = CH3, CO·NH2, CSjNH2, C6H5, C6H4NO2, C6H3(NO2)2, and CO·CH3) have been examined. Of the three possible isomeric reaction products, the true flavanone carbonyl derivatives I are predominantly obtained under acidic conditions with the less basic carbonyl reagents; alkaline conditions or strongly basic reagents give the pyrazolines III; the 2′-hydroxychalkone derivatives II may be prepared by the alkaline ring cleavage of the hetero ring of I.

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  • Recent advances of chroman-4-one derivatives: Synthetic approaches and bioactivities

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    Citation Excerpt :

    For example, Kállay et al. reported that the hydrazones of flavanone can be predominantly obtained under acidic conditions. In alkaline medium, the cleavage of the hetero ring of chromanone occurs to form the pyrazolines and the 2-hydroxychalcone derivatives [56]. However, we have prepared 3-(1H-1,2,4-triazol-1-yl)-chroman-4-one phenylhydrazone (98) from the reaction of corresponding chroman-4-one 90 and hydrochloride salt of phenylhydrazine in methanol at room temperature (Fig. 37).

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