Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions
Yükleniyor...
Dosyalar
Tarih
2016
Yazarlar
Ekiz, Makbule
Tutar, Ahmet
Ökten, Salih
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
The bromination of 2-aminobenzonitrile (2) with molecular bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile (7) in 98% yield. One-pot syntheses are described for dibromotacrine derivatives (6,14-18) utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine 6 and 15 by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of dibromo 6 and 15 derivatives with n-BuLi followed by trapping with an electrophile [Si(Me)(3)Cl, S-2(Me)(2)]. Both were converted to the corresponding cyano derivatives (21-23) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, respectively). Copper-induced nucleophilic substitution of dibromide 15 with NaOMe afforded mono methoxide 31 in 25% yield. (C) 2016 Elsevier Ltd. All rights reserved.
Açıklama
Okten, Salih/0000-0001-9656-1803; Tutar, Ahmet/0000-0001-5524-8001
WOS: 000381530900009
WOS: 000381530900009
Anahtar Kelimeler
Tacrine, Bromotacrine, Cyanotacrine, Lithium-bromine exchange, Thiomethyltacrine, Methoxytacrine
Kaynak
Tetrahedron
WoS Q Değeri
Q2
Scopus Q Değeri
Q2
Cilt
72
Sayı
35
