One-pot synthesis of α-acyloxyaminoamides via nitrones as imine surrogates in the Ugi MCR

被引：16

作者：

Basso, A ^{[1
]}

Banfi, L ^{[1
]}

Guanti, G ^{[1
]}

Riva, R ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 46期

关键词：

multicomponent reactions; Ugi reaction; hydroxylamines; nitrones; alpha-acyloxyaminoamides;

D O I：

10.1016/j.tetlet.2005.09.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-acyloxyaminoamides can be prepared, with yields ranging from fair to very good (up to 89%), through an Ugi four component reaction by mixing a carbonyl component, a carboxylic acid, an isocyanide and an N-alkylated hydroxylamine in methanol. Preformed nitrones furnish the same final compounds with comparable yields. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8003 / 8006

页数：4

共 16 条

[1] Synthesis of dibenzyl iminodiacetic derivatives as potential inhibitors of HIV-1 aspartyl protease [J].

Abalain, C ;

Langlois, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (02) :155-160

[2] A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].

Basso, A ;

Banfi, L ;

Riva, R ;

Guanti, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579

[3] Ugi multicomponent reaction with hydroxylamines: an efficient route to hydroxamic acid derivatives [J].

Basso, A ;

Banfi, L ;

Guanti, G ;

Riva, R ;

Riu, A .

TETRAHEDRON LETTERS, 2004, 45 (32) :6109-6111

[4] U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction [J].

Basso, A ;

Banfi, L ;

Riva, R ;

Guanti, G .

TETRAHEDRON LETTERS, 2004, 45 (03) :587-590

[5] Ammonium chloride promoted Ugi four-component, five-center reaction of α-substituted α-isocyano acetic acid:: A strong solvent effect [J].

Bonne, D ;

Dekhane, M ;

Zhu, JP .

ORGANIC LETTERS, 2004, 6 (25) :4771-4774

[6] AN IMPROVED SYNTHESIS OF KETONITRONES [J].

FRANCO, S ;

MERCHAN, FL ;

MERINO, P ;

TEJERO, T .

SYNTHETIC COMMUNICATIONS, 1995, 25 (15) :2275-2284

[7] RENIN INHIBITORS CONTAINING ISOSTERIC REPLACEMENTS OF THE AMIDE BOND CONNECTING THE P3 AND P2 SITES [J].

KALTENBRONN, JS ;

HUDSPETH, JP ;

LUNNEY, EA ;

MICHNIEWICZ, BM ;

NICOLAIDES, ED ;

REPINE, JT ;

ROARK, WH ;

STIER, MA ;

TINNEY, FJ ;

WOO, PKW ;

ESSENBURG, AD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :838-845

[8] PREPARATION AND ANTICONVULSANT ACTIVITY OF A SERIES OF FUNCTIONALIZED ALPHA-HETEROATOM-SUBSTITUTED AMINO-ACIDS [J].

KOHN, H ;

SAWHNEY, KN ;

LEGALL, P ;

ROBERTSON, DW ;

LEANDER, JD .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2444-2452

[9]

Lombardo M, 2000, SYNTHESIS-STUTTGART, P759

[10]

MODERHACK D, 1973, LIEBIGS ANN CHEM, P359

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