Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries

被引：76

作者：

Bhat, AS ^{[1
]}

Whetstone, JL ^{[1
]}

Brueggemeier, RW ^{[1
]}

机构：

[1] Ohio State Univ, Coll Pharm, Div Med Chem & Pharmacognosy, Columbus, OH 43210 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

benzopyrones; flavonoids; combinatorial chemistry; sonogashira coupling;

D O I：

10.1016/S0040-4039(99)00279-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2469 / 2472

页数：4

共 13 条

[1]

[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881

[2] Titanium mediated reductive amination on solid support: Extending the utility of the 4-hydroxy-thiophenol linker [J].

Breitenbucher, JG ;

Hui, HC .

TETRAHEDRON LETTERS, 1998, 39 (45) :8207-8210

[3] A PARADIGM FOR DRUG DISCOVERY EMPLOYING ENCODED COMBINATORIAL LIBRARIES [J].

BURBAUM, JJ ;

OHLMEYER, MHJ ;

READER, JC ;

HENDERSON, I ;

DILLARD, LW ;

LI, G ;

RANDLE, TL ;

SIGAL, NH ;

CHELSKY, D ;

BALDWIN, JJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (13) :6027-6031

[4] PREPARATIVE AND REGIOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF 2-HYDROXYARYL IODIDES WITH ETHYNYLARENES [J].

CIATTINI, PG ;

MORERA, E ;

ORTAR, G ;

ROSSI, SS .

TETRAHEDRON, 1991, 47 (32) :6449-6456

[5] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

LUNDELL, GF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KLING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246

[6] SYNTHESIS AND BINDING-PROPERTIES OF 2-AMINO-5-PHOSPHONO-3-PENTENOIC ACID PHOTOAFFINITY LIGANDS AS PROBES FOR THE GLUTAMATE RECOGNITION SITE OF THE NMDA RECEPTOR [J].

HECKENDORN, R ;

ALLGEIER, H ;

BAUD, J ;

GUNZENHAUSER, W ;

ANGST, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) :3721-3726

[7] 6-endo- and 5-exo-digonal cyclizations of o-hydroxyphenyl ethynyl ketones: A key step for highly selective benzopyranone formation [J].

Nakatani, K ;

Okamoto, A ;

Saito, I .

TETRAHEDRON, 1996, 52 (28) :9427-9446

[8] The current status of heterocyclic combinatorial libraries [J].

Nefzi, A ;

Ostresh, JM ;

Houghten, RA .

CHEMICAL REVIEWS, 1997, 97 (02) :449-472

[9]

Riva C, 1997, SYNTHESIS-STUTTGART, P195

[10] Synthesis and applications of small molecule libraries [J].

Thompson, LA ;

Ellman, JA .

CHEMICAL REVIEWS, 1996, 96 (01) :555-600

← 1 2 →