TY - JOUR
T1 - Synthesis of 5-azaindolizine derivatives by the palladium-catalyzed intermolecular formal [3+2] cycloaddition of alkylidenecyclopropanes with 1,2-diazines
AU - Siriwardana, Amal Inoka
AU - Nakamura, Itaru
AU - Yamamoto, Yoshinori
PY - 2004
Y1 - 2004
N2 - 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.
AB - 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.
UR - http://pubs.acs.org.ezproxy.lib.monash.edu.au/doi/pdf/10.1021/jo035800h?cookieSet=1
U2 - 10.1021/jo035810i
DO - 10.1021/jo035810i
M3 - Article
VL - 69
SP - 3202
EP - 3204
JO - The Journal of Organic Chemistry
JF - The Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -