Multi-component reactions between 2-aminopyrimidine, aldehydes and isonitriles: the use of a nonpolar solvent suppresses formation of multiple products

被引：80

作者：

Parchinsky, VZ ^{[1
]}

Shuvalova, O ^{[1
]}

Ushakova, O ^{[1
]}

Kravchenko, DV ^{[1
]}

Krasavin, M ^{[1
]}

机构：

[1] Chem Divers Res Inst, Chimki 114401, Moscow Reg, Russia

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

imidazo[1,2-a]pyrimidine; Ugi reaction; combinatorial chemistry; toluene; ammonium chloride;

D O I：

10.1016/j.tetlet.2005.11.152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reliable and convenient protocol for MCRs between 2-aminopyrimidine, aldehydes and isonitriles is described. Toluene was chosen as the reaction solvent based on mechanistic reasoning. The product mixtures were found to contain a single imidazo[1,2-a]pyrimidine product in each case, which were isolated and purified by precipitation and crystallization. Chromatographic recovery from filtrates raised the total yields to 49-66%. The procedure provides a practical alternative to hitherto reported methods in which formation of multiple products was observed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：947 / 951

页数：5

共 14 条

[1] IMIDAZO[1,2-B]PYRIDAZINES .12. SYNTHESES AND CENTRAL-NERVOUS-SYSTEM ACTIVITIES OF SOME SUBSTITUTED IMIDAZO[1,2-B]PYRIDAZINES AND RELATED IMIDAZO[1,2-A]PYRIDINES, IMIDAZO[1,2-A]PYRIMIDINES AND IMIDAZO[1,2-A]PYRAZINES
BARLIN, GB
DAVIES, LP
IRELAND, SJ
NGU, MML
ZHANG, JK
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (05) : 877 - 888
[2] Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO
[3] 2-R
[4] A three-component solid-phase synthesis of 3-aminoimidazo[1,2-a]azines
Blackburn, C
[J]. TETRAHEDRON LETTERS, 1998, 39 (31) : 5469 - 5472
[5] A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification
Cristau, P
Vors, JP
Zhu, JP
[J]. ORGANIC LETTERS, 2001, 3 (25) : 4079 - 4082
[6] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[7] 2-U
[8] Synthesis of polysubstituted 4,5,6,7-tetrahydrofuro[2,3-c]pyridines by a novel multicomponent reaction
Fayol, A
Zhu, JP
[J]. ORGANIC LETTERS, 2004, 6 (01) : 115 - 118
[9] Synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines by a novel three-component condensation
Groebke, K
Weber, L
Mehlin, F
[J]. SYNLETT, 1998, (06) : 661 - +
[10] Ammonium chloride-promoted four-component synthesis of pyrrolo[3,4-b]pyridin-5-one
Janvier, P
Sun, XW
Bienaymé, H
Zhu, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2560 - 2567

← 1 2 →