Regioselective two step synthesis of 3-substituted 2-aminoimidazo[1,2-a]pyrimidines

被引：34

作者：

Carballares, Santiago

Cifuentes, Marta M.

Stephenson, Gregory A.

机构：

[1] Lilly SA, Dept Invest, Madrid 28108, Spain

[2] Eli Lilly & Co, Xray Crystallog, Indianapolis, IN 46285 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 11期

关键词：

D O I：

10.1016/j.tetlet.2006.11.181

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two step procedure for the regioselective synthesis of 3-substituted-2-aminoimidazo[1,2-a]pyrimidines is described. The key step is a Dimroth rearrangement of a mixture of 2 and 3-substituted aminoimidazo[1,2-a]pyrimidines that yields quantitatively one regioisomer. Reaction screening for the rearrangement step is reported. A multicomponent isocyanide based reaction is chosen as the preferred way for the synthesis of the precursors. Elucidation of regiochemistry has been done by X-ray determination of some representative compounds. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2041 / 2045

页数：5

相关论文

共 44 条

[11] Synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines by a novel three-component condensation [J].

Groebke, K ;

Weber, L ;

Mehlin, F .

SYNLETT, 1998, (06) :661-+

[12] INVESTIGATION OF MINIMAL STRUCTURAL CONDITIONS FOR DIMROTH-TYPE REARRANGEMENT IN POLYAZAINDOLIZINE SERIES [J].

GUERRET, P ;

JACQUIER, R ;

MAURY, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (04) :643-&

[13] A novel application of the Ullmann coupling reaction for the alkylsulfenylation of 2-amino-imidazo[1,2-a]pyridine [J].

Hamdouchi, C ;

de Blas, J ;

Ezquerra, J .

TETRAHEDRON, 1999, 55 (02) :541-548

[14] Structure-based design of a new class of highly selective aminoimidazo[1,2-a]pyridine-based inhibitors of cyclin dependent kinases [J].

Hamdouchi, C ;

Zhong, B ;

Mendoza, J ;

Collins, E ;

Jaramillo, C ;

De Diego, JE ;

Robertson, D ;

Spencer, CD ;

Anderson, BD ;

Watkins, SA ;

Zhang, FM ;

Brooks, HB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1943-1947

[15] 2-amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imidazo-[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus:: Stereospecific synthesis and antiviral activity [J].

Hamdouchi, C ;

de Blas, J ;

del Prado, M ;

Gruber, J ;

Heinz, BA ;

Vance, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (01) :50-59

[16]

Hamdouchi C, 1998, SYNTHESIS-STUTTGART, P867

[17] Microwave-assisted multi-component synthesis of fused 3-aminoimidazoles [J].

Ireland, SM ;

Tye, H ;

Whittaker, M .

TETRAHEDRON LETTERS, 2003, 44 (23) :4369-4371

[18] INTERMEDIATES IN DIMROTH REARRANGEMENT OF IMIDAZO(1,2-A)PYRIDINES [J].

JACQUIER, R ;

LOPEZ, H ;

MAURY, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (05) :755-762

[19] Regioselective synthesis of 3,6-disubstituted-2-aminoimidazo[1,2-a]pyridines [J].

Jaramillo, C ;

Carretero, JC ;

de Diego, JE ;

del Prado, M ;

Hamdouchi, C ;

Roldán, JL ;

Sánchez-Martínez, C .

TETRAHEDRON LETTERS, 2002, 43 (50) :9051-9054

[20]

Jaramillo C, 2002, SYNLETT, P1544

← 1 2 3 4 5 →