6533b862fe1ef96bd12c76f8

RESEARCH PRODUCT

One-pot synthesis of polysubstituted indolizines by an addition/cycloaromatization sequence.

Till OpatzMurat Kucukdisli

subject

AldehydesMolecular StructureStereochemistryChemistryOrganic ChemistryOne-pot synthesisIndolizinesSequence (biology)KetonesDeprotonationCyclizationElectrophileNitrilesMichael reactionMolecule

description

Indolizines carrying various substituents in positions 5-8 were obtained from readily available 2-(1H-pyrrol-1-yl)nitriles and α,β-unsaturated ketones or aldehydes in a one-pot procedure. Michael addition of the deprotonated aminonitriles to the acceptors followed by acid-catalyzed electrophilic cyclization produces 5,6-dihydroindolizine-5-carbonitriles. From these stable intermediates, substituted indolizines were obtained via base-induced dehydrocyanation.

yearjournalcountryeditionlanguage
2013-06-14The Journal of organic chemistry
10.1021/jo400992nhttps://pubmed.ncbi.nlm.nih.gov/23735100