Intra- and intermolecular (3++2) cycloadditions of aldehyde or ketohydrazones.
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概要
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The reaction of several 2-(alkenyloxy)benzaldehydes (or 1-naphthaldehydes) (1) with arylhydrazine hydrochlorides leads to intramolecular [3<SUP>+</SUP>+2] cycloadducts, 3-substituted 2-aryl-1,2,3,3a,4,9b(or 1,2,3,3a,4,11c)hexahydro[1]benzopyrano (or naphtho[1′,2′:5,6]pyrano)[4,3-<I>c</I>]pyrazole hydrochlorides (4), in good yields. Free bases (5) were obtained in high yields after the treatment of 4 with triethylamine. The thermal treatment of 5 at 150 °C gave 3-substituted 2-aryl-2,3,3a,4-tetrahydro[1]benzopyrano(or naphtho[1′,2′:5,6]pyrano)[4,3-<I>c</I>]pyrazoles. The reaction of 1 with methylhydrazine sulfate gave the corresponding 2-methyl derivatives. Analogous intramolecular [3<SUP>+</SUP>+2] cycloadducts were obtained from the reaction of 2′-(alkenyloxy)acetophenones with arylhydrazine hydrochlorides. Intermolecular [3<SUP>+</SUP>+2] cycloadducts were also obtained from a reaction mixture of 1-naphthaldehyde, arylhydrazine hydrochlorides, and styrene.
- 公益社団法人 日本化学会の論文
著者
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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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Shimizu Tomio
Department of Dyeing, Faculty of Industrial Arts, Kyoto Technical University
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Nakano Mineo
Department of Color Chemistry and Technology, Faculty of Industrial Arts, Kyoto Technical University
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