Preparation of quinolines from resin-bound esters using titanium reagents

被引：11

作者：

Macleod, C

Austin, CA

Hamprecht, DW

Hartley, RC ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] GlaxoSmithKline, Ctr Ric, I-37135 Verona, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

Quinolines; titanium and compounds; solid-phase synthesis; thioacetals; Wittig reaction;

D O I：

10.1016/j.tetlet.2004.09.170

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

ortho-Amino homobenzylic thioacetals are prepared from ortho-nitrobenzaidehydes via homologation using an alpha-methoxy Wittig reagent. Titanium reagents are generated from the 1,3-dithianes using a low valent titanium reagent and are then used to alkylidenate resin-bound esters. An N-silylated Boc group protects the ortho-amino functionality. Traceless SPS of quinolines is completed by treating the resulting resin-bound enol ethers with TFA and then oxidizing with manganese dioxide to give 2-substituted quinolines in high purity without the need for chromatography. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8879 / 8882

页数：4

共 30 条

[1] Traceless solid-phase organic synthesis
Blaney, P
Grigg, R
Sridharan, V
[J]. CHEMICAL REVIEWS, 2002, 102 (07) : 2607 - 2624
[2] The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles
Bräse, S
Gil, C
Knepper, K
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) : 2415 - 2437
[3] Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines
Cho, CS
Kim, BT
Choi, HJ
Kim, TJ
Shim, SC
[J]. TETRAHEDRON, 2003, 59 (40) : 7997 - 8002
[4] Solid-phase syntheses of furopyridine and furoquinoline systems
Cironi, P
Tulla-Puche, J
Barany, G
Albericio, F
Alvarez, M
[J]. ORGANIC LETTERS, 2004, 6 (09) : 1405 - 1408
[5] New synthetic pathway to diverse 2-substituted quinolines based on a multicomponent reaction: Solution-phase and solid-phase applications
Demaude, T
Knerr, L
Pasau, P
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05): : 768 - 775
[6] Comprehensive survey of combinatorial library synthesis: 2003
Dolle, RE
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05): : 623 - 679
[7] Comprehensive survey of combinatorial library synthesis: 2002
Dolle, RE
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (06): : 693 - 753
[8] Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids
Du, W
[J]. TETRAHEDRON, 2003, 59 (44) : 8649 - 8687
[9] Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas
Du, W
Curran, DP
[J]. ORGANIC LETTERS, 2003, 5 (10) : 1765 - 1768
[10] Traceless and multifunctional linkers for the generation of small molecules on solid supports
Gil, C
Bräse, S
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (03) : 230 - 237

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