Yenice, IşılBaşçeken, SinanBalcı, Metin2019-05-132019-05-132017Yenice, I., Başçeken, S., Balcı, M. (2017). Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties. Beilstein Journal of Organic Chemistry, 13, 825-834.1860-5397https://doi.org/10.3762/bjoc.13.83https://hdl.handle.net/11491/1746Intramolecular nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N-alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with hydrazine afforded the 6-exo-dig/6-endo-dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with iodine only resulted in the formation of the 6-endo-dig cyclization product regardless of the substitution of the alkyne functionality. © 2017 Yenice et al.enAttribution 4.0 International (CC BY 4.0)info:eu-repo/semantics/openAccessAlkyne CyclizationPyrrolePyrrolooxazinonePyrrolopyrazinonePyrrolotriazinoneArticle1382583410.3762/bjoc.13.83N/AQ2