A traceless solid-phase synthesis of 1,4-diazepan-2-ones

被引：4

作者：

Saruta, Kunio ^{[1
]}

Ogiku, Tsuyoshi ^{[1
]}

机构：

[1] Mitsubishi Tanabe Pharma Corp, Med Chem Lab, Yodogawa Ku, Osaka 5328505, Japan

来源：

CHEMISTRY LETTERS | 2008年 / 37卷 / 08期

关键词：

D O I：

10.1246/cl.2008.820

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel synthesis of 1,4-diazepan-2-ones using a traceless solid-phase approach is described, in which many kinds of 1,4-diazepan-2-one have been efficiently obtained in high purity. The strategy is based on intramolecular alkylation of tertiary amines, followed by elimination of the desired tertiary amines from the generated quarternary ammonium salts.

引用

页码：820 / 821

页数：2

共 27 条

[1] Application of Grignard reagents to the synthesis of tertiary methylamines via resin-bound oxyiminium ions [J].

Blaney, P ;

Grigg, R ;

Rankovic, Z ;

Thoroughgood, M .

TETRAHEDRON LETTERS, 2000, 41 (34) :6639-6642

[2] Solid-phase synthesis of tertiary methylamines via reductive alkylation-fragmentation using a hydroxylamine linker [J].

Blaney, P ;

Grigg, R ;

Rankovic, Z ;

Thoroughgood, M .

TETRAHEDRON LETTERS, 2000, 41 (34) :6635-6638

[3] Synthesis of tertiary amines using a polystyrene (REM) resin [J].

Brown, AR ;

Rees, DC ;

Rankovic, Z ;

Morphy, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3288-3295

[4] Vapor-phase Hofmann elimination: A rapid one-pot method for the cleavage of tertiary amines from radio frequency encoded solid-phase synthesis [J].

Brown, AR .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (04) :283-285

[5] Natural products - The future scaffolds for novel antibiotics? [J].

Butler, MS ;

Buss, AD .

BIOCHEMICAL PHARMACOLOGY, 2006, 71 (07) :919-929

[6] A novel traceless solid phase tertiary amine synthesis based on Merrifield resin [J].

Cai, JQ ;

Wathey, B .

TETRAHEDRON LETTERS, 2001, 42 (07) :1383-1385

[7] 4-ALKYL-(OR ARALKYL) 1-ARYL-2-PIPERAZINONES [J].

FANCHER, OE ;

HAYAO, S ;

STRYCKER, WG .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (02) :154-&

[8] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].

FUKUYAMA, T ;

JOW, CK ;

CHEUNG, M .

TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374

[9] General combinatorial synthesis of tertiary amines on solid support. A novel conditional release strategy based on traceless linking at nitrogen [J].

Gustafsson, M ;

Olsson, R ;

Andersson, CM .

TETRAHEDRON LETTERS, 2001, 42 (01) :133-136

[10] Homologs of 1,2,5-hexahydro-3-one-1H-1,4-diazepine (DAP) as novel dipeptidomimetics and molecular scaffolds:: Efficient preparation of synthons [J].

Han, YL ;

Mierke, DF ;

Chorev, M .

BIOPOLYMERS, 2002, 64 (01) :1-15

← 1 2 3 →