The high-pressure SNAr reaction of N-p-fluorobenzyl-2-chlorobenzimidazole with amines;: an approach to norastemizole and analogues

被引：32

作者：

Barrett, IC ^{[1
]}

Kerr, MA ^{[1
]}

机构：

[1] Acadia Univ, Dept Chem, Wolfville, NS B0P 1X0, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(99)00290-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-p-fluorobenzyl-2-chlorobenzimidazole was treated under hyperbaric conditions with a variety of primary and secondary amines. The resulting SNAr reaction proceeded smoothly to produce excellent yields of adducts in most cases. This methodology provides rapid access to astemizole, norastemizole and related analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2439 / 2442

页数：4

共 6 条

[1] AROMATIC FLUORINE COMPOUNDS .11. REPLACEMENT OF CHLORINE BY FLUORINE IN HALOPYRIDINES [J].

FINGER, GC ;

DICKERSON, DRF ;

HAMER, J ;

STARR, LD ;

GUTOWSKY, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1666-&

[2] Palladium catalyzed amination of 2-chloro-1,3-azole derivatives: Mild entry to potent H-1-antihistaminic norastemizole [J].

Hong, YP ;

Tanoury, GJ ;

Wilkinson, HS ;

Bakale, RP ;

Wald, SA ;

Senanayake, CH .

TETRAHEDRON LETTERS, 1997, 38 (32) :5607-5610

[3]

ISAACS NS, 1997, HIGH PRESSURE TECHNI, P308

[4]

JANSSENS FE, 1992, Patent No. 0232937

[5]

RAMACHANDRAN PS, 1994, J ORG CHEM, V59, P4341

[6] Nickel-catalyzed amination of aryl chlorides [J].

Wolfe, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) :6054-6058

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