First synthesis of methyl 3-amino-4-(het)aryl-1H-pyrrole-2-carboxylates as useful scaffolds in medicinal chemistry

被引：9

作者：

Rochais, C ^{[1
]}

Lisowski, V ^{[1
]}

Dallemagne, P ^{[1
]}

Rault, S ^{[1
]}

机构：

[1] Univ Caen, UFR Sci Pharmaceut, CERMN, F-14032 Caen, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 10期

关键词：

aminoarylypyrrolecarboxylates; enamine; diethyl-aminomalonate; cyclisation;

D O I：

10.1016/j.tet.2004.01.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of new methyl 4-(het)aryl-3-amino-1H-pyrrole-2-carboxylates was achieved starting from commercial arylacetonitriles. This four steps synthesis afforded with good yields interesting building-blocks useful in the access to many nitrogen heterocycles with potential therapeutic interest. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2267 / 2270

页数：4

共 12 条

[1]

ALTMANN E, 1997, Patent No. [09749706, 9749706]

[2] A short, facile synthesis of 5-substituted 3-amino-1H-pyrrole-2-carboxylates [J].

Chen, N ;

Lu, YL ;

Gadamasetti, K ;

Hurt, CR ;

Norman, MH ;

Fotsch, C .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2603-2605

[3] Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds [J].

Chun, BK ;

Song, GY ;

Chu, CK .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4852-4858

[4]

ELLIOT AJ, 1997, J ORG CHEM, V52, P8071

[5] Improved syntheses of 3H,5H-pyrrolo[3,2-d]pyrimidines [J].

Furneaux, RH ;

Tyler, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8411-8412

[6] SYNTHESIS OF 3-AMINOTHIOPHENES FROM ARYL ACETONITRILE AND HETARYL ACETONITRILE [J].

KIRSCH, G ;

CAGNIANT, D ;

CAGNIANT, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :443-445

[7] NEW SYNTHESIS OF PYRROLO[3,2-D]PYRIMIDINES (9-DEAZAPURINES) VIA 3-AMINO-2-CARBOALKOXYPYRROLES [J].

LIM, MI ;

KLEIN, RS ;

FOX, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3826-3829

[8]

Lisowski V, 2002, SYNTHESIS-STUTTGART, P753

[9] Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents [J].

Lisowski, V ;

Enguehard, C ;

Lancelot, JC ;

Caignard, DH ;

Lambel, S ;

Leonce, S ;

Pierre, A ;

Atassi, G ;

Renard, P ;

Rault, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (16) :2205-2208

[10] Structure-activity relationships of a series of pyrrolo[3,2-d]pyrimidine derivatives and related compounds as neuropeptide Y5 receptor antagonists [J].

Norman, MH ;

Chen, N ;

Chen, ZD ;

Fotsch, C ;

Hale, C ;

Han, NH ;

Hurt, R ;

Jenkins, T ;

Kincaid, J ;

Liu, LB ;

Lu, YL ;

Moreno, O ;

Santora, VJ ;

Sonnenberg, JD ;

Karbon, W .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4288-4312

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