SYNTHETIC APPLICATIONS OF 2-ARYL-4-PIPERIDONES .10. SYNTHESIS OF 3-AMINOPIPERIDINES, POTENTIAL SUBSTANCE-P ANTAGONISTS

被引：21

作者：

DIEZ, A

VOLDOIRE, A

LOPEZ, I

RUBIRALTA, M

SEGARRA, V

PAGES, L

PALACIOS, JM

机构：

[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN

[2] LABS ALMIRALL SA,E-08024 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 17期

关键词：

D O I：

10.1016/0040-4020(95)98710-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method is described for the synthesis of 3-aminopiperidines from 4-piperidones based on a KOEt treatment of the tostylate of the corresponding oximes (Neber rearrangement). The procedure is applied to the synthesis of N-benzyl-3-amino-4,4-diethoxypiperidine (13), (R)-N-(2-hydroxy-1-phenyl)ethyl analogues 18, and 2-phenyl derivatives 27-28. The methoxybenzylation of the primary amino group of these aminopiperidines leads to a series of potential substance P antagonists.

引用

页码：5143 / 5156

页数：14

共 19 条

[1]

Diez, Mavel, Teulade, Chavignon, Sinibaldi, Troin, Rubiralta, Heterocycles, 36, pp. 2451-2463, (1993)

[2]

de Costa, Dominguez, He, Williams, Radesca, Bowen, J. Med. Chem., 35, pp. 4334-4343, (1992)

[3]

Knapp, Hae, J. Org. Chem., 58, pp. 2650-2651, (1993)

[4]

Pearson, Bergmeier, Williams, J. Org. Chem., 57, pp. 3977-3987, (1992)

[5]

Hua, Parck, Katsukira, Bharathi, J. Org. Chem., 58, pp. 2144-2150, (1993)

[6]

Pearson, Bergmeier, Williams, J. Org. Chem., 57, pp. 3977-3987, (1992)

[7]

Desai, Lefkowitz, Tetrahedron Lett., 35, pp. 4701-4704, (1994)

[8]

Lowe, Drugs Future, 17, pp. 1115-1121, (1992)

[9]

Desai, Lefkowitz, Thadeio, Longo, Snider, J. Med. Chem., 35, pp. 4911-4913, (1992)

[10]

Desai, Thadeio, Lefkowitz, Tetrahedron Lett., 34, pp. 5831-5834, (1993)

← 1 2 →