671183-80-5Relevant academic research and scientific papers
Nucleophilic Addition to Electron-Rich Heteroaromatics: Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides
Clayden, Jonathan,Turnbull, Rachel,Pinto, Ivan
, p. 609 - 611 (2007/10/03)
(Matrix presented) Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.
