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Chemoselectivity and Conformational Analysis of the Reaction of 2-Acetylcycloalkanones with Benzohydrazide: Synthesis and Reduction of 1-Aroylcycloalkapyrazole Derivatives

✍ Scribed by Constantinos A. Tsoleridis; Julia Stephanidou-Stephanatou; Chara Zika; Minothora Pozarentzi; Stephanos Alevizopoulos

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
214 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

From the reaction of 2‐acetylcyclopentanone and 2‐acetyl‐2‐methylcyclopentanone with benzohydrazide, the 1‐benzoyl‐6a‐hydroxycyclopentapyrazole derivatives 2a and 2b were obtained as the only reaction products, whereas from the reaction of 2‐acetylcyclohexanone an epimeric cis/trans mixture of the 2‐benzoyl‐3‐hydroxy‐2__H__‐indazole derivative 3c was formed. The dehydration of the isolated compounds 2a and 3c, as well as the NaBH~4~ and NaBH~3~CN reduction products of 2a were studied. The structural assignments of the compounds derived were established by analysis of their NMR spectra (^1^H, ^13^C, DEPT, COSY, NOESY, HETCOR CH, and COLOC CH). The chemoselectivity of the reactions of 1a and 1c with benzohydrazide was studied by conformational analysis with MM2 and semiempirical (AM1 and PM3) MO calculations.

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