Simple and facile reduction of azides to amines:: synthesis of DNA interactive pyrrolo[2,1-c][1,4]benzodiazepines

被引：38

作者：

Kamal, A ^{[1
]}

Reddy, PSMM ^{[1
]}

Reddy, DR ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 37期

关键词：

amines; reductive cyclization; hydriodic acid; pyrrolobenzodiazepines;

D O I：

10.1016/S0040-4039(02)01453-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of aromatic azido compounds to the corresponding amines with hydriodic acid has been investigated and found to result in high yields. This reductive methodology which proceeds under non refluxing condition has been extended for the synthesis of DNA-interactive pyrrolo[2,1-c][1,4] benzodiazepine antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6629 / 6631

页数：3

共 17 条

[1] AMINOBOROHYDRIDES .8. A FACILE REDUCTION OF ALIPHATIC AND BENZYLIC AZIDES TO THE CORRESPONDING AMINES IN HIGH-YIELD AND PURITY USING LITHIUM N,N-DIMETHYLAMINOBOROHYDRIDE [J].

ALVAREZ, SG ;

FISHER, GB ;

SINGARAM, B .

TETRAHEDRON LETTERS, 1995, 36 (15) :2567-2570

[2] HEXAMETHYLDISILATHIANE - ITS USE IN THE CONVERSION OF AROMATIC AND HETEROAROMATIC AZIDES TO AMINES [J].

CAPPERUCCI, A ;

DEGL'INNOCENTI, A ;

FUNICELLO, M ;

MAURIELLO, G ;

SCAFATO, P ;

SPAGNOLO, P .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2254-2256

[3] Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity [J].

Gregson, SJ ;

Howard, PW ;

Hartley, JA ;

Brooks, NA ;

Adams, LJ ;

Jenkins, TC ;

Kelland, LR ;

Thurston, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (05) :737-748

[4] Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine [J].

Huang, Y ;

Zhang, YM ;

Wang, YL .

TETRAHEDRON LETTERS, 1997, 38 (06) :1065-1066

[5]

ITO M, 1995, SYNTHESIS-STUTTGART, P376

[6] Iodotrimethylsilane: A mild and efficient reagent for the reduction of azides to amines [J].

Kamal, A ;

Rao, NV ;

Laxman, E .

TETRAHEDRON LETTERS, 1997, 38 (39) :6945-6948

[7] Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST [J].

Kamal, A ;

Reddy, BSP ;

Reddy, BSN .

TETRAHEDRON LETTERS, 1996, 37 (37) :6803-6806

[8]

Kamal Ahmed, 2002, Current Medicinal Chemistry - Anti-Cancer Agents, V2, P215, DOI 10.2174/1568011023354119

[9]

KRASNEC L, 1971, Z CHEM, V11, P110

[10] Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: reduction with hydriodic acid revisited [J].

Kumar, JSD ;

Ho, MM ;

Toyokuni, T .

TETRAHEDRON LETTERS, 2001, 42 (33) :5601-5603

← 1 2 →