Tetrahedron p. 449 - 460 (1999)
Update date:2022-08-03
Topics:
Boukamcha
Gharbi
Martin
Chiaroni
Mighri
Khemiss
1,3-Dipolar cycloaddition reaction of 2-diazopropane 1 with diarylidenencetones 2 carried out at 0°C led to a minor Δ2-pyrazoline monocycloadduct 4 and two diastereoisomeric bicycloadducts 5 and 6. The same addition realised at -60°C has enabled us to observe, beside bis-Δ2- pyrazolines 5 and 6, the formation of unexpected Δ3(1,3,4)oxadiazoline derivatives 9 and 10. These two diastereoisomers result from the addition of 2-diazopropane on the carbonyl of unstable Δ1-pyrazoline intermediates 3' and 3'' with an unusual regiochemical way. Oxidation of 5 and 6 gave 3H- pyrazoles 7 and 8.
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