Palladium-catalyzed vinylation of haloazulenes and halotropolones with olefins. Utility of the heck reaction in the conjugated carbon chain preparation.

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概要

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• The reactions of 3-iodotropolone with styrenes (styrene, <I>p</I>-methoxystyrene, and 2-vinylpyridine), methyl acrylate, and allylic compounds (methyl 3-butenoate, 3-butenenitrile, 1-allyl-3,4-dimethoxybenzene, and 1-allyl-3,4-methylenedioxybenzene) were carried out, according to the modified Heck's procedure, to give 3-styryl-, 3-(2-carboxyvinyl)-, and 3-(3-substituted 1-propenyl)tropolones, respectively. Similarly, 4-bromo- or 5-bromotropolone was made to react with these olefins to yield 4-styryltropolone or the corresponding 5-(2-substituted vinyl)- and 5-(3-substituted 1-propenyl)tropolones. Substitution of 2-chlorotropone by styrenes produced 2-styryltropones. Extension of the vinylation to 2-amino-6-bromoazulenes, ethyl 3-bromo-1-azulenecarboxylate, and diethyl 2-chloro-1,3-azulenedicarboxylate resulted in a similar substitution.

• 公益社団法人 日本化学会の論文

著者

• Inoue Naoto

  Department Of Cardiology Kyoto Second Red Cross Hospital

• Horino Hiroshi

  Department Of Chemistry Graduate School Of Science Tohoku University

• Asao Toyonobu

  Department of Chemistry Faculty of Science Tohoku University

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