Triazolopyridines. Part 8.1 Nucleophilic substitution reactions of 5-bromo[1,2,3]triazolo[5,1-a]isoquinoline and 7-bromo[1,2,3]-triazolo[1,5-a]pyridine
作者:Belen Abarca、Fatemeh Mojarred、Gurnos Jones、Caroline Phillips、Nadine Ng、Jonathan Wastling
DOI:10.1016/s0040-4020(88)90040-3
日期:1988.1
5-bromotriazoloisoquinoline (3) and of 7-bromo-3-methyltriazolopyridine (6) proceeds readily to give a range of 5-substituted triazoloisoquinolines (4a)-(4e), and of 7-substituted triazolopyridines (7a)-(7h) respectively. Triazoloisoquinolines have been converted into 1,3-disubstituted isoquinolines (11)-(13), (15), and (16), and triazolopyridines into 2,6-disubstituted pyridines (17)-(19). Of secondary amine
5-溴三唑并异喹啉(3)和7-溴-3-甲基三唑并吡啶(6)的亲核取代反应容易进行,从而得到一系列5-取代的三唑并喹啉(4a)-(4e)和7-取代的三唑并吡啶(7a)- (7h)。三唑异喹啉已被转化为1,3-二取代的异喹啉(11)-(13),(15)和(16),三唑并吡啶已转化为2,6-二取代的吡啶(17)-(19)。在仲胺亲核试剂中,仅哌啶与7-溴-3-甲基三唑并吡啶(6)反应,得到7-取代的衍生物(7g)。该反应中的第二种产物是2,6-二取代的吡啶(8)。当使用吗啉或N-乙酰基哌嗪时,类似的化合物(20)-(24)是唯一的产物。7-溴三唑并吡啶(9)与哌啶或吗啉的反应可高收率地得到2,