3-Acylaminopyrazole derivatives via a regioselectively N-protected 3-nitropyrazole

被引：5

作者：

Orsini, P ^{[1
]}

Traquandi, G ^{[1
]}

Sansonna, P ^{[1
]}

Pevarello, P ^{[1
]}

机构：

[1] Nerviano Med Sci, BU Oncol, Dept Chem, I-20014 Nerviano, MI, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 06期

关键词：

3-aminopyrazole; 3-acylaminopyrazole; 3-nitropyrazole;

D O I：

10.1016/j.tetlet.2004.12.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple procedure for the selective protection of the enclocyclic 1-N of 3-aminopyrazoles as tert-butoxycarbamate (Boc) in good yield is described. A 3-nitropyrazole derivative represents the key intermediate with the nitro substituent determining the regiochemistry of the obtained protected Compound. Subsequent acylation at the exocyclic amino group gave rise, after Bee removal, to a series of 3-acylaminopyrazoles in high yields and purities. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：933 / 935

页数：3

共 11 条

[1]

BRINKMEYER RS, 1989, J HETEROCYCLIC CHEM, V26, P1713

[2] REACTIONS WITH DIAZOAZOLES .8. SYNTHESES OF AZOLO[5,1-D]-1,2,3,5-TETRAZIN-4(3H)-ONES [J].

EGE, G ;

GILBERT, K ;

MAURER, K .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (08) :1375-1395

[3]

ELNAGDI MH, 1983, HETEROCYCLES, V20, P2437

[4] 3-aminopyrazole inhibitors of CDK2/cyclin A as antitumor agents. 1. Lead finding [J].

Pevarello, P ;

Brasca, MG ;

Amici, R ;

Orsini, P ;

Traquandi, G ;

Corti, L ;

Piutti, C ;

Sansonna, P ;

Villa, M ;

Pierce, BS ;

Pulici, M ;

Giordano, P ;

Martina, K ;

Fritzen, EL ;

Nugent, RA ;

Casale, E ;

Cameron, A ;

Ciomei, M ;

Roletto, F ;

Isacchi, A ;

Fogliatto, G ;

Pesenti, E ;

Pastori, W ;

Marsiglio, A ;

Leach, KL ;

Clare, PM ;

Fiorentini, F ;

Varasi, M ;

Vulpetti, A ;

Warpehoski, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (13) :3367-3380

[5]

PEVARELLO P, Patent No. 2001012189

[6]

PEVARELLO P, Patent No. 2002048114

[7]

Puello JQ, 1997, TETRAHEDRON, V53, P10783

[8] Selective ring N-protection of aminopyrazoles [J].

Seelen, W ;

Schäfer, M ;

Ernst, A .

TETRAHEDRON LETTERS, 2003, 44 (24) :4491-4493

[9] Cancer cell cycles [J].

Sherr, CJ .

SCIENCE, 1996, 274 (5293) :1672-1677

[10] A MILD OXIDATION OF AROMATIC-AMINES [J].

WEBB, KS ;

SENEVIRATNE, V .

TETRAHEDRON LETTERS, 1995, 36 (14) :2377-2378

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