Solid-phase synthesis of N-alkyl-N-(β-keto)amides and 1,2,4,5-tetrasubstituted imidazoles using a traceless cleavage strategy

被引：54

作者：

Lee, HB ^{[1
]}

Balasubramanian, S ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 03期

关键词：

D O I：

10.1021/ol991271l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The solid-phase synthesis of N-alkyl-N-(beta-keto)amides and 1,2,4,5-tetrasubstituted imidazoles was demonstrated using a traceless cleavage strategy based on benzylic acylammonium chloride reactivity, The approach enables the assembly of diverse compounds in a minimal number of steps in moderate to excellent yield (23-88%) and high purity (64-100%).

引用

收藏

页码：323 / 326

页数：4

相关论文

共 13 条

[1] AN ORALLY BIOAVAILABLE HIV-1 PROTEASE INHIBITOR CONTAINING AN IMIDAZOLE-DERIVED PEPTIDE-BOND REPLACEMENT - CRYSTALLOGRAPHIC AND PHARMACOKINETIC ANALYSIS [J].

ABDELMEGUID, SS ;

METCALF, BW ;

CARR, TJ ;

DEMARSH, P ;

DESJARLAIS, RL ;

FISHER, S ;

GREEN, DW ;

IVANOFF, L ;

LAMBERT, DM ;

MURTHY, KHM ;

PETTEWAY, SR ;

PITTS, WJ ;

TOMASZEK, TA ;

WINBORNE, E ;

ZHAO, BG ;

DREYER, GB ;

MEEK, TD .

BIOCHEMISTRY, 1994, 33 (39) :11671-11677

[2] Synthesis of an array of amides by aluminium chloride assisted cleavage of resin-bound esters [J].

Barn, DR ;

Morphy, JR ;

Rees, DC .

TETRAHEDRON LETTERS, 1996, 37 (18) :3213-3216

[3] Solid-supported reagent strategies for rapid purification of combinatorial synthesis products [J].

Booth, RJ ;

Hodges, JC .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (01) :18-26

[4]

COOLEY JH, 1989, SYNTHESIS-STUTTGART, P1

[5] Reactivity of benzylic acylammonium chlorides. A novel method for the synthesis of N-phenacylamides. [J].

Coskun, N ;

Tirli, F .

SYNTHETIC COMMUNICATIONS, 1997, 27 (01) :1-9

[6] Organic chemistry on solid supports [J].

Fruchtel, JS ;

Jung, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42

[7] Linkers for solid phase organic synthesis [J].

James, IW .

TETRAHEDRON, 1999, 55 (16) :4855-4946

[8] PREPARATION AND CHARACTERIZATION OF CRYSTALLINE N-ACYLAMMONIUM SALTS [J].

KING, JA ;

BRYANT, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5136-5139

[9] Mild N-dealkylation of tertiary, benzylic amines with acid chlorides: Application to solid-phase chemistry [J].

Miller, MW ;

Vice, SF ;

McCombie, SW .

TETRAHEDRON LETTERS, 1998, 39 (21) :3429-3432

[10]

SHULTS EE, 1993, ZH ORG KHIM+, V29, P1149