Intramolecular 1,3-dipolar cycloaddition of nitrilimines bearing alkenyl groups.
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概要
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The reaction of the arylhydrazones of some 2-(alkenyloxy)benzaldehydes(or 1-naphthaldehydes) with Pb(OAc)<SUB>4</SUB> leads, <I>via</I> the nitrilimine intermediates, to intramolecular 1,3-dipolar cycloadducts, 3-substituted 2-aryl-2,3,3a,4-tetrahydro[1]benzopyrano(or naphtho[1′,2′:5,6]pyrano)[4,3-<I>c</I>]pyrazoles, in 10–80% yields. In the presence of an excess of Pb(OAc)<SUB>4</SUB>, these cycloadducts were dehydrogenated to 3-substituted 2-aryl-2,4-dihydro[1]benzopyrano(or naphtho[1′,2′:5,6]pyrano)[4,3-<I>c</I>]pyrazoles. In the presence of a large excess of Pb(OAc)<SUB>4</SUB>, some of the pyrazoles were acetoxylated to give the corresponding 4-acetoxypyrazoles. The effect of substituents of the alkenyl group on reactivity of the reaction was interpreted in terms of the frontier molecular orbital (FMO) theory.
著者
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Ishikawa Susumu
Department Of Cardiac Surgery Austin & Repatriation Medical Centre University Of Melbourne
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Teramura Kazuhiro
Department Of Pathology Wakakusa Dai-ichi Hospital
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Hayashi Yoshiyuki
Department Of Acoustic Design Kyusyu Institute Of Design
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Ishikawa Susumu
Department of Dyeing, Faculty of Industrial Arts, Kyoto Technical University
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Shimizu Tomio
Department of Dyeing, Faculty of Industrial Arts, Kyoto Technical University
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