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Synthesis 1997; 1997(12): 1495-1498
DOI: 10.1055/s-1997-1369
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A New and Efficient Synthesis of Pyridazin-3(2H)-ones via 1,3-Dipolar Cycloaddition

Moncef Msaddek1 , Mohamed Rammah1 , Kabula Ciamala2 , Joël Vebrel2 , Bernard Laude2
  • 1Département de Chimie, Faculté des Sciences et Techniques, Université du Centre, Route de Kairouan, 5000 Monastir, Tunisia
  • 2Laboratoire de Chimie et Electrochimie Moléculaire, Faculté des Sciences et Techniques, 16 Route de Gray, F-25030 Besançon, France
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Publication Date:
31 December 2000 (online)

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3-Arylidenebenzofuran-2(3H)-ones are obtained by condensation of aldehydes Ar1CHO with benzofuran-2(3H)-one. A mixture of stereoisomers (Z) and (E) was isolated. The reaction of diarylnitrilimines with the Z+E mixture or with each stereoisomer leads regio- and stereoselectively to cycloadducts which give, after acidic treatment, the same 5,6-diaryl-4-(o-hydroxyphenyl)pyridazin-3(2H)-one 6, irrespective of the double bond geometry of the starting olefin.

Acidic treatment of cycloadducts 4 and 5 gives quantitatively the pyridazin-3(2-H)-ones 6