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Synthesis of nitrogen heterocycles by condensation of the conjugate base of open‐chain reissert compound analogs with vinyltriphenylphosphonium bromide (schweizer's salt)
Author(s) -
Cooney John V.,
Beaver Bruce D.,
Mcewen William E.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220304
Subject(s) - chemistry , wittig reaction , conjugate , reagent , bromide , salt (chemistry) , intramolecular force , amide , combinatorial chemistry , base (topology) , condensation , condensation reaction , organic chemistry , catalysis , mathematical analysis , physics , mathematics , thermodynamics
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.