Reaction of azides with dichloroindium hydride: Very mild production of amines and pyrrolidin-2-imines through possible indium-aminyl radicals

被引：67

作者：

Benati, Luisa ^{[1
]}

Bencivenni, Giorgio ^{[1
]}

Leardini, Rino ^{[1
]}

Nanni, Daniele ^{[1
]}

Minozzi, Matteo ^{[1
]}

Spagnolo, Piero ^{[1
]}

Scialpi, Rosanna ^{[1
]}

Zanardi, Giuseppe ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol0606637

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. gamma-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

引用

页码：2499 / 2502

页数：4

共 70 条

[51]

Ranu BC, 2003, SYNTHESIS-STUTTGART, P1012

[52] Use of indium hydride (Cl2InH) for chemoselective reduction of the carbon-carbon double bond in conjugated alkenes [J].

Ranu, BC ;

Samanta, S .

TETRAHEDRON LETTERS, 2002, 43 (41) :7405-7407

[53]

Ranu BC, 2000, EUR J ORG CHEM, V2000, P2347

[54] A novel, simple, chemoselective and practical protocol for the reduction of azides using In/NH4Cl [J].

Reddy, GV ;

Rao, GV ;

Iyengar, DS .

TETRAHEDRON LETTERS, 1999, 40 (20) :3937-3938

[55]

Renaud P., 2001, RADICALS ORGANIC SYN

[56]

RENAUD P, 2000, RADICALS ORGANIC SYN, V1

[57] EFFICIENT REDUCTION OF AZIDES TO AMINES WITH TRIBUTYLSTANNANE - HIGH-YIELD SYNTHESES OF AMINO AND DIAMINO DEOXYNUCLEOSIDES [J].

SAMANO, MC ;

ROBINS, MJ .

TETRAHEDRON LETTERS, 1991, 32 (44) :6293-6296

[58] Tin-free radical allylation of B-alkylcatecholboranes [J].

Schaffner, AP ;

Renaud, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (23) :2658-2660

[59] Evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase [J].

Shankaran, K ;

Donnelly, KL ;

Shah, SK ;

Guthikonda, RN ;

MacCoss, M ;

Humes, JL ;

Pacholok, SG ;

Grant, SK ;

Kelly, TM ;

Wong, KK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (17) :4539-4544

[60] Catalytic generation of indium hydride in a highly diastereoselective reductive aldol reaction [J].

Shibata, I ;

Kato, H ;

Ishida, T ;

Yasuda, M ;

Baba, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) :711-714

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