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

[11] Radical chain reactions of α-azido ketones with tributyltin hydride:: reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals [J].

Benati, L ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Spagnolo, P ;

Strazzari, S ;

Zanardi, G ;

Calestani, G .

TETRAHEDRON, 2002, 58 (18) :3485-3492

[12] Radical chain reactions of α-azido-β-keto esters with tributyltin hydride.: A novel entry to amides and lactams through regiospecific nitrogen insertion [J].

Benati, L ;

Nanni, D ;

Sangiorgi, C ;

Spagnolo, P .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7836-7841

[13] On the reduction of S-alkyl-thionocarbonates (Xanthates) with phosphorus compounds [J].

Boivin, J ;

Jrad, R ;

Juge, S ;

Nguyen, VT .

ORGANIC LETTERS, 2003, 5 (10) :1645-1648

[14] Indium-mediated mild and facile method for the synthesis of amides [J].

Cho, DH ;

Jang, DO .

TETRAHEDRON LETTERS, 2004, 45 (11) :2285-2287

[15] Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: Homolytic allylation at nitrogen [J].

Dang, HS ;

Roberts, BP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (13) :1493-1498

[16] REACTION OF BENZOYL AZIDE WITH TRIBUTYLTIN HYDRIDE [J].

FRANKEL, M ;

WAGNER, D ;

GERTNER, D ;

ZILKHA, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 7 (03) :518-&

[17] Tin-free radical sequences under acidic conditions. Convergent access to azole-containing structures [J].

Gagosz, F ;

Zard, SZ .

ORGANIC LETTERS, 2002, 4 (24) :4345-4348

[18] A new tin-free source of amidyl radicals [J].

Gagosz, F ;

Moutrille, C ;

Zard, SZ .

ORGANIC LETTERS, 2002, 4 (16) :2707-2709

[19]

Gotov B, 2002, SYNLETT, P361

[20] 2-iminopyrrolidines as potent and selective inhibitors of human inducible nitric oxide synthase [J].

Hagen, TJ ;

Bergmanis, AA ;

Kramer, SW ;

Fok, KF ;

Schmelzer, AE ;

Pitzele, BS ;

Swenton, L ;

Jerome, GM ;

Kornmeier, CM ;

Moore, WM ;

Branson, LF ;

Connor, JR ;

Manning, PT ;

Currie, MG ;

Hallinan, EA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (19) :3675-3683

← 1 2 3 4 5 6 7 →