Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe-0-FeCl3 or CuCl-TMEDA

被引：69

作者：

Benedetti, M ^{[1
]}

Forti, L ^{[1
]}

Ghelfi, F ^{[1
]}

Pagnoni, UM ^{[1
]}

Ronzoni, R ^{[1
]}

机构：

[1] UNIV MODENA,DIPARTIMENTO CHIM,I-41100 MODENA,ITALY

来源：

TETRAHEDRON | 1997年 / 53卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(97)00908-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe-0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：14031 / 14042

页数：12

共 92 条

[1] ANDRES C, 1996, TETRAHEDRON LETT, P9085
[2] First total synthesis of pyrrolam A
Aoyagi, Y
Manabe, T
Ohta, A
Kurihara, T
Pang, GL
Yuhara, T
[J]. TETRAHEDRON, 1996, 52 (03) : 869 - 876
[3] CHLORINE-ACTIVATION BY REDOX-TRANSFER .3. ABNORMAL ADDITION OF CHLOROFORM TO OLEFINS
ASSCHER, M
VOFSI, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (AUG): : 3921 - &
[4] REDOX TRANSFER .V. ELEMENTARY STEPS . OXIDATION OF FERROUS AND CUPROUS CHLORIDE BY CARBON TETRACHLORIDE
ASSCHER, M
VOFSI, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (09): : 947 - &
[5] CHLORINE ACTIVATION BY REDOX TRANSFER .2. ADDITION OF CARBON TETRACHLORIDE TO OLEFINS
ASSCHER, M
VOFSI, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAR): : 1887 - &
[6] A NEW RADICAL-BASED SYNTHESIS OF LACTAMS AND INDOLONES FROM DITHIOCARBONATES (XANTHATES)
AXON, J
BOITEAU, L
BOIVIN, J
FORBES, JE
ZARD, SZ
[J]. TETRAHEDRON LETTERS, 1994, 35 (11) : 1719 - 1722
[7] 3-oxa- and 3-azabicyclo[3.1.0]hexan-2-ones via tandem radical cyclization-intramolecular S(N)2 reactions
Baldovini, N
Bertrand, MP
Carriere, A
Nouguier, R
Plancher, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3205 - 3208
[8] BARTH F, 1990, TETRAHEDRON LETT, P1121
[9] BELLESIA F, 1997, SYNTHETIC COMMUN, P961
[10] STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED ALPHA-IODOAMIDES - SYNTHESIS OF ENANTIOPURE PYRROLIDINES AND TRANSITION-STATE MODELING
BELVISI, L
GENNARI, C
POLI, G
SCOLASTICO, C
SALOM, B
VASSALLO, M
[J]. TETRAHEDRON, 1992, 48 (19) : 3945 - 3960

← 1 2 3 4 5 6 7 8 9 10 →