Cascade synthesis of pyrido[3,2-a]indolizines by reaction of Kröhnke–Mukaiyama salts with malononitrile dimer

Abstract

An efficient protocol for the synthesis of highly functionalized 2-aminoindolizines and pyrido[3,2-a]indolizines has been achieved via the reaction of N-RC(O)CH2-2-chloropyridinium bromides with 2-amino-1,1,3-tricyanopropene in the presence of Et3N. The reaction of N-allyl-2-chloropyridinium bromide with 2-amino-1,1,3-tricyanopropene in the presence of Et3N gives 3-[1-allylpyridin-2(1Н)-ylidene]-2-aminoprop-1-ene-1,1,3-tricarbonitrile, which could be cyclized to give [2-amino-(2-amino-3-vinylindolizin-1-yl)methylene]malononitrile upon treatment with KOH–DMF.