Facile cyclization of amidyl radicals generated from N-acyltriazenes

被引:38
作者
Lu, HJ [1 ]
Li, CZ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2005.07.023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Acyltriazenes serve as a tin-free and initiator-free source for amidyl radicals. Thermal decomposition of N,N'-diaryl-N-(4-pentenoyl)triazenes in refluxing toluene led to the formation of monocyclic and tricyclic lactams in satisfactory yields via 5-exo amidyl radical cyclization. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5983 / 5985
页数:3
相关论文
共 19 条
[1]   PHOTOCHEMICAL TRANSFORMATIONS .16. A NOVEL SYNTHESIS OF LACTONES [J].
BARTON, DHR ;
BECKWITH, AL ;
GOOSEN, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :181-&
[2]   IMINYL, AMIDYL, AND CARBAMYL RADICALS FROM O-BENZOYL OXIMES AND O-BENZOYL HYDROXAMIC ACID-DERIVATIVES [J].
BOIVIN, J ;
CALLIERDUBLANCHET, AC ;
QUICLETSIRE, B ;
SCHIANO, AM ;
ZARD, SZ .
TETRAHEDRON, 1995, 51 (23) :6517-6528
[3]  
CAMPBELL TW, 1951, CHEM REV, V48, P299
[4]   Cyclization or hydrogen migration: Theoretical study and experimental evidence on the reactivities of unsaturated amidyl radicals [J].
Chen, Q ;
Shen, MH ;
Tang, Y ;
Li, CZ .
ORGANIC LETTERS, 2005, 7 (08) :1625-1627
[5]   1,3 ACYL MIGRATIONS IN THERMAL DECOMPOSITION OF N-ACYLTRIAZENES [J].
CURTIN, DY ;
DRULINER, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (05) :1552-&
[6]   N-ACYL-N-ALKYLCARBAMOYLOXY RADICALS - ENTRIES TO AMIDYL RADICALS BY DECARBOXYLATION AND TO ALPHA-AMIDE RADICALS BY RADICAL TRANSLOCATION [J].
ESKER, JL ;
NEWCOMB, M .
TETRAHEDRON LETTERS, 1992, 33 (40) :5913-5916
[7]   THE GENERATION OF NITROGEN RADICALS AND THEIR CYCLIZATIONS FOR THE CONSTRUCTION OF THE PYRROLIDINE NUCLEUS [J].
ESKER, JL ;
NEWCOMB, M .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 58, 1993, 58 :1-45
[8]   AMIDYL RADICALS FROM N-(PHENYLTHIO)AMIDES [J].
ESKER, JL ;
NEWCOMB, M .
TETRAHEDRON LETTERS, 1993, 34 (43) :6877-6880
[9]   Free radical cyclizations involving nitrogen [J].
Fallis, AG ;
Brinza, IM .
TETRAHEDRON, 1997, 53 (52) :17543-17594
[10]   A new tin-free source of amidyl radicals [J].
Gagosz, F ;
Moutrille, C ;
Zard, SZ .
ORGANIC LETTERS, 2002, 4 (16) :2707-2709