Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines

被引：35

作者：

Kiselyov, AS ^{[1
]}

Smith, L ^{[1
]}

机构：

[1] Small Mol Drug Discovery, Chem Divers, San Diego, CA 92121 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 15期

关键词：

one-pot reactions; pyrazolo[1,5-a]pyrimidines; imidazo[1,2-a]pyrimidines; alpha; beta-unsaturated imines; condensations;

D O I：

10.1016/j.tetlet.2006.02.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have described a convenient regioselective one-pot approach to pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidine derivatives from alpha,beta-unsaturated imines generated in situ and amino heterocycles. Reaction is general with respect to all three components, namely (i) nitrile, (ii) aldehyde, and (iii) amino heterocycle reagents. Good yields (52-77%), convenient isolation of the targeted molecules are the distinct characteristics of the developed protocol. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2611 / 2614

页数：4

共 24 条

[1] Effect of YM529 on a model of mandibular invasion by oral squamous cell carcinoma in mice [J].

Cui, NH ;

Nomura, T ;

Noma, H ;

Yokoo, K ;

Takagi, R ;

Hashimoto, S ;

Okamoto, M ;

Sato, M ;

Yu, GY ;

Guo, CB ;

Shibahala, T .

CLINICAL CANCER RESEARCH, 2005, 11 (07) :2713-2719

[2] 2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis:: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR [J].

Enguehard-Gueiffier, C ;

Fauvelle, F ;

Debouzy, JC ;

Peinnequin, A ;

Thery, I ;

Dabouis, V ;

Gueiffier, A .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2005, 24 (2-3) :219-227

[3] Procedure for the parallel preparation of 3-imidazo[1,2-a]pyridin-3-yl-propionic acid derivatives involving Meldrum's acid [J].

Gerencsér, J ;

Panka, G ;

Nagy, T ;

Egyed, O ;

Dormán, G ;

Ürge, L ;

Darvas, F .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (04) :530-538

[4] Design, synthesis, computational and biological evaluation of new anxiolytics [J].

Geronikaki, A ;

Babaev, E ;

Dearden, J ;

Dehaen, W ;

Filimonov, D ;

Galaeva, I ;

Krajneva, V ;

Lagunin, A ;

Macaev, F ;

Molodavkin, G ;

Poroikov, V ;

Pogrebnoi, S ;

Saloutin, V ;

Stepanchikova, A ;

Stingaci, E ;

Tkach, N ;

Vlad, L ;

Voronina, T .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (24) :6559-6568

[5] 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

[6]

Harrison TS, 2005, CNS DRUGS, V19, P65

[7] Hypervalent iodine(III) sulfonate mediated synthesis of imidazo[1,2-a]pyridines [J].

Huang, HY ;

Hou, RS ;

Wang, HM ;

Chen, LC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2004, 51 (06) :1377-1380

[8] Potent 1,3,4-trisubstituted pyrrolidine CCR5 receptor antagonists: effects of fused heterocycles on antiviral activity and pharmacokinetic properties [J].

Kim, D ;

Wang, LP ;

Hale, JJ ;

Lynch, CL ;

Budhu, RJ ;

MacCross, M ;

Mills, SG ;

Malkowitz, L ;

Gould, SL ;

DeMartino, JA ;

Springer, MS ;

Hazuda, D ;

Miller, M ;

Kessler, J ;

Hrin, RC ;

Carver, G ;

Carella, A ;

Henry, K ;

Lineberger, J ;

Schleif, WA ;

Emini, EA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (08) :2129-2134

[9] A novel three-component reaction of N-fluoropyridinium salts:: a facile approach to imidazo[1,2-a]pyridines [J].

Kiselyov, AS .

TETRAHEDRON LETTERS, 2005, 46 (26) :4487-4490

[10] One-pot synthesis of polysubstituted pyrimidines [J].

Kiselyov, AS .

TETRAHEDRON LETTERS, 2005, 46 (10) :1663-1665

← 1 2 3 →