Synthesis of 5-azaindolizine derivatives by the palladium-catalyzed intermolecular formal [3+2] cycloaddition of alkylidenecyclopropanes with 1,2-diazines

Amal Inoka Siriwardana, Itaru Nakamura, Yoshinori Yamamoto

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Abstract

The palladium-catalyzed formal [3+2] cycloaddition reaction of alkylidenecyclopropanes with 1,2-diazines proceeded smoothly to give the corresponding 5-azaindolizine derivatives in good to allowable yields. For example, in the presence of 5 mol of Pd(PPh3)(4), the reaction of 1-propyl-hexylidenecyclopropane with phthalazine or with pyridazine proceeded at 120 degreesC without solvent, and the corresponding 2-(1-butylpentyl)pyrrolo[2,1-a]phthalazine or 6-(1-butylpentyl)pyrrolo[1,2-b]pyridazine was obtained in 61 or 49 yield, respectively.
Original languageEnglish
Pages (from-to)3202 - 3204
Number of pages3
JournalThe Journal of Organic Chemistry
Volume69
Issue number9
DOIs
Publication statusPublished - 2004
Externally publishedYes

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