Collect. Czech. Chem. Commun.
1984, 49, 533-542
https://doi.org/10.1135/cccc19840533
1,3-Dipolar cycloadditions of N-(5-nitro-2-furfuryl)isoquinolinium bromide in the synthesis of benzoindolizines
Jarmila Štetinová, Jaroslav Kováč, František Považanec, Miloslava Dandárová and Alžbeta Pajchortová
Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava
Abstract
Substituted 3-(5-nitro-2-furyl)benzo[g]indolizines III-XII were synthesized by a 1,3-dipolar cycloaddition of the ylide II formed in situ from N-(5-nitro-2-furfuryl)isoquinolinium bromide (I) and dimethyl butinedioate, diethyl butenedioate, 1-nitro-2-phenylethylene, ethyl 2-propenoate, ethyl 3-(5-nitro-2-furyl)-2-propenoate, 1,3-diphenyl-2-propenone, 1,3-diphenyl-2-propinone, 2-propenenitrile, 1-phenyl-3-(5-nitro-2-furyl)-2-propenone, and methyl 2-cyano-3-(4-nitrophenyl)-2-propenoate. Structure of these products was verified by spectral evidence.
