Regioselective cleavage of O-benzyl-N-arylamidoximes:: synthesis of N-aryl amidines and amidoximes

被引：14

作者：

Anbazhagan, M ^{[1
]}

Boykin, DW ^{[1
]}

Stephens, CE ^{[1
]}

机构：

[1] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 50期

基金：

美国国家卫生研究院;

关键词：

O-benzylamidoximes; amidines; amidoximes; Pd/C/EtOH; HBr/HOAc;

D O I：

10.1016/S0040-4039(02)02289-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O-Benzyl-N-arylamidoximes have been regioselectively deprotected to provide either N-aryl amidines or amidoximes. As a result, the targeted compounds can now be prepared using palladium-catalyzed N-arylation chemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9089 / 9092

页数：4

共 25 条

[1] Palladium-catalyzed N-arylation of O-methylamidoximes [J].

Anbazhagan, M ;

Stephens, CE ;

Boykin, DW .

TETRAHEDRON LETTERS, 2002, 43 (23) :4221-4224

[2]

ANDREWS MJ, 1978, INDIAN J CHEM B, V16, P465

[3] NITROSOAZOMETHINE DERIVATIVES . OXIDATION OF AMIDOXIMES [J].

BOYER, JH ;

FRINTS, PJA .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (12) :4554-&

[4] Anti-pneumocystis activity of bis-amidoximes and bis-O-alkylamidoximes prodrugs [J].

Boykin, DW ;

Kumar, A ;

Hall, JE ;

Bender, BC ;

Tidwell, RR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (24) :3017-3020

[5] SOME HYDROXYAMIDINES AND AMIDOXIMES [J].

BRIGGS, LH ;

CAMBIE, RC ;

DEAN, IC ;

RUTLEDGE, PS .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (02) :357-366

[6]

BROWN GR, 1982, SYNTHESIS-STUTTGART, P1036

[7] N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase:: Structure-activity studies and demonstration of in vivo activity [J].

Collins, JL ;

Shearer, BG ;

Oplinger, JA ;

Lee, SL ;

Garvey, EP ;

Salter, M ;

Duffy, C ;

Burnette, TC ;

Furfine, ES .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (15) :2858-2871

[8]

Fevig JM, 1999, ANNU REP MED CHEM, V34, P81

[9] NITRILE OXIDES .6. SOME NOVEL ADDITION REACTIONS OF AROMATIC NITRILE OXIDES [J].

GRUNDMAN.C ;

FROMMELD, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :157-&

[10] NITRILE OXIDES .V. STABLE AROMATIC NITRILE OXIDES [J].

GRUNDMANN, C ;

DEAN, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2809-+

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