Pyrazolo[1,5-a]pyridines: synthetic approaches to a novel class of antiherpetics

被引:55
作者
Johns, BA
Gudmundsson, KS
Turner, EM
Allen, SH
Jung, DK
Sexton, CJ
Boyd, FL
Peel, MR
机构
[1] GlaxoSmithKline Res & Dev Ltd, Dept Med Chem, Res Triangle Pk, NC 27709 USA
[2] GlaxoSmithKline Res & Dev Ltd, Dept Virol, Res Triangle Pk, NC 27709 USA
关键词
pyrazolo[1,5-a]pyridine; alkynyl ketone; pyrimidine synthesis; HSV;
D O I
10.1016/j.tet.2003.02.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of a novel class of 7-amino-3-pyrimidinyl-pyrazolo[1,5-a]pyridine antiherpetic compounds is described. The synthetic methodology is designed to allow for rapid analog synthesis around the C-3 and C-7 positions of the pyrazolo[1,5-a]pyridine. The 7-chloropyrazolo[1,5-a]pyridine D, produced through an azirine rearrangement, served as a key building block. Two complementary methodologies for construction of the C-3 pyrimidine are described. These methods include the development of a novel cyclization utilizing alkynyl ketones or enones to give highly substituted pyrimidines. The outlined strategies facilitated late stage manipulation of either the C-3 or C-7 positions providing flexibility for rapid analog synthesis. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9001 / 9011
页数:11
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