The design of efficient and selective routes to pyridyl analogues of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

被引：11

作者：

Barfoot, Christopher W. ^{[1
]}

Brown, Pamela ^{[1
]}

Dabbs, Steven ^{[1
]}

Davies, David T. ^{[1
]}

Hennessy, Alan J. ^{[1
]}

Miles, Timothy J. ^{[1
]}

Pearson, Neil D. ^{[2
]}

机构：

[1] GlaxoSmithKline Inc, Infect Dis CEDD, Antibacterial Discovery Performance Unit, Stevenage SG1 2NY, Herts, England

[2] GlaxoSmithKline Inc, Infect Dis CEDD, Antibacterial Discovery Performance Unit, Collegeville, PA 19426 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 38期

关键词：

CYCLIZATION;

D O I：

10.1016/j.tetlet.2010.07.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Letter describes the synthetic routes to challenging pyridyl analogues of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde which were key intermediates for our antibacterial medicinal chemistry programme. All routes described started from kojic acid (8) and have been used to give multigram quantities of each aldehyde. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5038 / 5040

页数：3

共 12 条

[1]

Axten J.M., 2004, [No title captured], Patent No. [WO2004058144, 2004058144]

[2]

Cailleau N., 2007, [No title captured], Patent No. [WO2,007,081,597, 2007081597]

[3] SUBSTITUTED DIHYDROBENZOPYRAN AND DIHYDROBENZOFURAN THIAZOLIDINE-2,4-DIONES AS HYPOGLYCEMIC AGENTS [J].

CLARK, DA ;

GOLDSTEIN, SW ;

VOLKMANN, RA ;

EGGLER, JF ;

HOLLAND, GF ;

HULIN, B ;

STEVENSON, RW ;

KREUTTER, DK ;

GIBBS, EM ;

KRUPP, MN ;

MERRIGAN, P ;

KELBAUGH, PL ;

ANDREWS, EG ;

TICKNER, DL ;

SULESKE, RT ;

LAMPHERE, CH ;

RAJECKAS, FJ ;

KAPPELER, WH ;

MCDERMOTT, RE ;

HUTSON, NJ ;

JOHNSON, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :319-325

[4]

David DD, 2002, WIPO patent, Patent No. [WO2002056882, 2002056882]

[5]

DOBROWSKY A, 1951, MONATSH CHEM, V82, P122, DOI 10.1007/BF01044198

[6] SYNTHESIS AND ANTIMICROBIAL INVESTIGATION OF THIAZOLINOALKYL-4(1H)-PYRIDONES [J].

EROL, DD ;

YULUG, N .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (11) :893-897

[7]

Lütjens H, 1999, SYNLETT, P1079

[8] A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines [J].

Murata, M ;

Buchwald, SL .

TETRAHEDRON, 2004, 60 (34) :7397-7403

[9] SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 5-(2-DODECYLPHENYL)-4,6-DITHIANONANEDIOIC ACID AND 5-[2-(8-PHENYLOCTYL)PHENYL]-4,6-DITHIANONANEDIOIC ACID - PROTOTYPES OF A NOVEL CLASS OF LEUKOTRIENE ANTAGONISTS [J].

PERCHONOCK, CD ;

MCCARTHY, ME ;

ERHARD, KF ;

GLEASON, JG ;

WASSERMAN, MA ;

MUCCITELLI, RM ;

DEVAN, JF ;

TUCKER, SS ;

VICKERY, LM ;

KIRCHNER, T ;

WEICHMAN, BM ;

MONG, S ;

CROOKE, ST ;

NEWTON, JF .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (09) :1145-1147

[10]

Sasamoto M., 1960, CHEM PHARM BULL, V8, P324

← 1 2 →