A new and efficient synthesis of pyridazin-3(2H)-ones via 1,3-dipolar cycloaddition

Article abstract of DOI:10.1055/s-1997-1369

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 and stereoselectively to cycloadducts which give, after acidic treatment, the same 5,6-diaryl-4-(0-hydroxyphenyl)pyridazin-3(2H)-one 6, irrespective of the double bond geometry of the starting olefin.

Full text of DOI:10.1055/s-1997-1369

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Synthesis 1997; 1997(12): 1495-1498
DOI: 10.1055/s-1997-1369
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-Arylidenebenzofuran-2(3H)-ones are obtained by condensation of
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aldehydes Ar CHO 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.
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Acidic treatment of cycloadducts 4 and 5 gives quantitatively the pyridazin-
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