Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties
Yükleniyor...
Dosyalar
Tarih
2017
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Erişim Hakkı
Attribution 4.0 International (CC BY 4.0)
info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
Özet
Intramolecular 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.
Açıklama
Anahtar Kelimeler
Alkyne Cyclization, Pyrrole, Pyrrolooxazinone, Pyrrolopyrazinone, Pyrrolotriazinone
Kaynak
Beilstein Journal of Organic Chemistry
WoS Q Değeri
N/A
Scopus Q Değeri
Q2
Cilt
13
Sayı
Künye
Yenice, 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.
