124552-73-4Relevant academic research and scientific papers
TRITHIOCYCLOPROPENIUM ION AS A BUILDING BLOCK FOR NITROGEN HETEROCYCLE SYNTHESIS
Yoshida, Zen-ichi,Hirai, Hideo,Miki, Sadao,Yoneda, Shigeo
, p. 3217 - 3232 (1989)
A new methodology for heterocycle synthesis using trithiocyclopropenium salt as a building block is described.Tris(tert-butylthio)cyclopropenium perchlorate (1) reacts with β-amino acids under basic conditions to give 1,2-dihydropyridines, where cyclopropenium salt serves as the three carbon homologator in heterocyclic ring formation.The selective syntheses of 1,5-benzodiazepines and benzimidazoles from 1 are also described.Reaction of 1 with o-phenylenediamines in dimethylformamide gives 1,5-benzodiazepines as a single product but in methanol benzimidazoles.The selective formation of 1,5-benzodiazepines and benzimidazoles could be accounted for by the solvent participation in the cyclization step.
