An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents

被引：26

作者：

Wang, Ying ^{[1
]}

Sarris, Kathy ^{[1
]}

Sauer, Daryl R. ^{[1
]}

Djuric, Stevan W. ^{[1
]}

机构：

[1] Abbott Labs, Global Pharmaceut Res & Dev, Med Chem Technol, High Throughput Organ Synth Grp, Abbott Pk, IL 60064 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 30期

关键词：

D O I：

10.1016/j.tetlet.2007.05.158

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylsulfonamides can be rapidly and conveniently synthesized from a variety of carboxylic acids and sulfonamides utilizing the commercially available reagents, PS-DCC and DMAP under mild reaction conditions. DMAP can be efficiently scavenged by utilization of a silica-supported tosic acid cartridge (Si-SCX). In most of the cases studied, products with high purities and yields were obtained without the need for further purification. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5181 / 5184

页数：4

共 19 条

[1] POTENT, SELECTIVE, WATER-SOLUBLE BENZODIAZEPINE-BASED CCKB RECEPTOR ANTAGONISTS THAT CONTAIN LIPOPHILIC CARBOXYLATE SURROGATES [J].

CHAMBERS, MS ;

HOBBS, SC ;

GRAHAM, MI ;

WATT, AP ;

FLETCHER, SR ;

BAKER, R ;

FREEDMAN, SB ;

PATEL, S ;

SMITH, AJ ;

MATASSA, VG .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (20) :2303-2308

[2] POLYMER-BOUND EDC (P-EDC) - A CONVENIENT REAGENT FOR FORMATION OF AN AMIDE BOND [J].

DESAI, MC ;

STRAMIELLO, LMS .

TETRAHEDRON LETTERS, 1993, 34 (48) :7685-7688

[3] CONVENIENT PROCEDURE FOR THE PREPARATION OF ALKYL AND ARYL SUBSTITUTED N-(AMINOALKYLACYL)SULFONAMIDES [J].

DRUMMOND, JT ;

JOHNSON, G .

TETRAHEDRON LETTERS, 1988, 29 (14) :1653-1656

[4]

Flynn DL, 1998, MED CHEM RES, V8, P219

[5]

IAN P, 2003, J ORG CHEM, V68, P9678

[6]

Ishizuka N, 2000, SYNTHESIS-STUTTGART, P784

[7] Facile synthesis of 5′-(N-acyl sulfonamide) derivatized nucleosides [J].

Johnson, DC ;

Widlanski, TS .

TETRAHEDRON LETTERS, 2001, 42 (22) :3677-3679

[8] Acyl sulfonamide anti-proliferatives: Benzene substituent structure -activity relationships for a novel class of antitumor agents [J].

Lobb, KL ;

Hipskind, PA ;

Aikins, JA ;

Alvarez, E ;

Cheung, YY ;

Considine, EL ;

De Dios, A ;

Durst, GL ;

Ferritto, R ;

Grossman, CS ;

Giera, DD ;

Hollister, BA ;

Huang, ZP ;

Iversen, PW ;

Law, KL ;

Li, TC ;

Lin, HS ;

Lopez, B ;

Lopez, JE ;

Cabrejas, LMM ;

McCann, DJ ;

Molero, V ;

Reilly, JE ;

Richett, ME ;

Shih, C ;

Teicher, B ;

Wikel, JH ;

White, WT ;

Mader, MM .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (22) :5367-5380

[9] Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives [J].

Mader, MM ;

Shih, C ;

Considine, E ;

De Dios, A ;

Grossman, CS ;

Hipskind, PA ;

Lin, FS ;

Lobb, KL ;

Lopez, B ;

Lopez, JE ;

Cabrejas, LMM ;

Richett, ME ;

White, WT ;

Cheung, YY ;

Huang, ZP ;

Reilly, JE ;

Dinn, SR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :617-620

[10]

PELLETIER JC, 1995, SYNLETT, P1141

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