Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions

被引：38

作者：

Barreto, Angelica de Fatima S. ^{[1
]}

Vercillo, Otilie E. ^{[1
]}

Birkett, Mike A. ^{[2
]}

Caulfield, John C. ^{[2
]}

Wessjohann, Ludger A. ^{[3
]}

Andrade, Carlos Kleber Z. ^{[1
]}

机构：

[1] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet LaQMOS, BR-70910970 Brasilia, DF, Brazil

[2] Ctr Sustainable Pest & Dis Management, Biol Chem Dept, Harpenden AL5 2JQ, Herts, England

[3] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 14期

关键词：

ONE-POT; MULTICOMPONENT REACTIONS; ORGANIC SYNTHESES; CLICK CHEMISTRY; DESIGN; MACROCYCLIZATIONS; OLIGOMERS; FIT;

D O I：

10.1039/c1ob05471f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of N-alkylglycines (peptoids) can be efficiently prepared via Ugi reactions using microwave irradiations. The results confirm the versatility and efficiency of the methodology for the preparation of functionalized peptoids. The products can be used in consecutive Ugi reactions to yield cyclic peptoids of potential biological interest.

引用

页码：5024 / 5027

页数：4

共 44 条

[11] Expedient synthesis and design strategies for new peptoid construction [J].

Gorske, BC ;

Jewell, SA ;

Guerard, EJ ;

Blackwell, HE .

ORGANIC LETTERS, 2005, 7 (08) :1521-1524

[12] Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support [J].

Holub, JM ;

Jang, HJ ;

Kirshenbaum, K .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (08) :1497-1502

[13] Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers [J].

Holub, Justin M. ;

Jang, Hangjun ;

Kirshenbaum, Kent .

ORGANIC LETTERS, 2007, 9 (17) :3275-3278

[14] Microwave Multicomponent Synthesis [J].

Hugel, Helmut M. .

MOLECULES, 2009, 14 (12) :4936-4972

[15] A simple, cheap alternative to 'designer convertible isonitriles' expedited with microwaves [J].

Hulme, Christopher ;

Chappeta, Shashi ;

Dietrich, Justin .

TETRAHEDRON LETTERS, 2009, 50 (28) :4054-4057

[16] An efficient solution phase synthesis of triazadibenzoazulenones: 'designer isonitrile free' methodology enabled by microwaves [J].

Hulme, Christopher ;

Chappeta, Shashi ;

Griffith, Chris ;

Lee, Yeon-Sun ;

Dietrich, Justin .

TETRAHEDRON LETTERS, 2009, 50 (17) :1939-1942

[17] Click to fit: Versatile polyvalent display on a peptidomimetic scaffold [J].

Jang, HJ ;

Fafarman, A ;

Holub, JM ;

Kirshenbaum, K .

ORGANIC LETTERS, 2005, 7 (10) :1951-1954

[18] Microwave-Assisted Multicomponent Reactions in the Heterocyclic Chemistry [J].

Jiang, Bo ;

Shi, Feng ;

Tu, Shu-Jiang .

CURRENT ORGANIC CHEMISTRY, 2010, 14 (04) :357-378

[19] Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

[20]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO

← 1 2 3 4 5 →