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Unusual reaction of N-aroyldihydrocyclopenta-pyrazolidinol with ketenes: formation of 1,3,4-oxadiazoles

✍ Scribed by Constantinos A Tsoleridis; Julia Stephanidou-Stephanatou; Petros Gounaridis; Hara Zika; Minodora Pozarentzi

Book ID: 104205333
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 431 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00633-1

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✦ Synopsis

1-Benzoyl-5-hydroxy-pyrazoline 1 was prepared and its reactions with ketenes, prepared in situ from the corresponding acid chlorides 3a -3d and the mixed anhydride 4, were studied. In all cases the 1,3,4-oxadiazoles 5 were isolated. In the case of compounds 3c and 3d a second diastereomeric oxadiazole 6 was obtained. In the case of 3a,3b and 4, an interesting aroyl migration product 7 was isolated. Structural assignments of the derived compounds were established by analysis of their IR, MS and NMR spectra ( 1 H, 13 C, COSY, NOESY, HETCOR and COLOC). The proposed reaction mechanism is supported by semi-empirical (AM1) MO calculations.

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## Abstract magnified image The reaction of 3‐formylchromone‐__N__‐benzoylhydrazone with ketenes, prepared __in situ__ from the corresponding acid chlorides **2a‐d** and the mixed anhydride **2e** was studied. In all cases 2‐(4′‐oxo‐4′__H__‐3′‐chromyl)‐5‐phenyl‐2,3‐dihydro‐1,3,4‐oxadiazoles (**3**

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## Abstract magnified image The compounds 5,6‐dihydro‐4__H__‐imidazo[4,5‐__c__][1,2,5]oxadiazole (**3a**, RH), 4,6,10,12‐tetramethyl‐5,6,11,12‐tetrahydro‐4__H__,10__H__‐bis(1,2,5)oxadiazolo[3,4‐__d__:3′,4′‐__I__][1,3,6,8]tetraazecine (**4b**, RCH~3~), __N__^3^,__N__^3^′‐methylenebis‐3,4‐diamino‐