77270-16-7Relevant academic research and scientific papers
Synthesis of Nitrogen Heterocycles by Condensation of the Conjugate Base of Open-Chain Reissert Compound Analogs with Vinyltriphenylphosphonium Bromide (Schweizer's Salt)
Cooney, John V.,Beaver, Bruce D.,McEwen, William E.
, p. 635 - 642 (2007/10/02)
Reaction of the conjugate base of several open-chain Reissert compound analogs with vinyltriphenylphosphonium bromide is shown to afford a convenient route to substituted pyrroles.The condensation is a two-step process involving an initial reversible addition to form an unstabilized Wittig reagent followed by an intramolecular Wittig reaction upon the carbonyl group of the tertiary amide functionality with concomitant elimination of HCN.Several applications to the synthesis of 1,2,5-trisubstituted pyrroles are presented, together with attempts to expand this methodology to the synthesis of other heterocyclic systems.
Synthesis of Substituted Pyrroles by Intramolecular Condensation of a Wittig Reagent with the Carbonyl Group of a Tertiary Amide
Cooney, John V.,McEwen, William E.
, p. 2570 - 2573 (2007/10/02)
1,2,5-Trisubstituted pyrroles are obtained in 50-100percent yields by addition of the conjugate bases of open-chain analogues of Reissert compounds to the vinyltriphenylphosphonium cation, with subsequent cyclization by an intramolecular Wittig reaction and base-catalyzed elimination of hydrogen cyanide.
