Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions
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Dosyalar
Tarih
2016
Yazarlar
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
