Tin-free radical sequences under acidic conditions. Convergent access to azole-containing structures

被引：63

作者：

Gagosz, F ^{[1
]}

Zard, SZ ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Organ Synth Lab, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 24期

关键词：

D O I：

10.1021/ol0270024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic Various xanthates add efficiently to olefins bearing [1,2,4]triazole, imidazole, or benzimidazole moieties in the presence of camphorsulfonic acid via a radical chain reaction initiated by a small amount of lauroyl peroxide. The adducts may be transformed to more complex molecules by implementing a further radical cyclization.

引用

页码：4345 / 4348

页数：4

共 28 条

[1] Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles [J].

Aldabbagh, F ;

Bowman, WR ;

Mann, E ;

Slawin, AMZ .

TETRAHEDRON, 1999, 55 (26) :8111-8128

[2] Synthesis of heterocycles by radical cyclisation [J].

Aldabbagh, F ;

Bowman, WR .

CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04) :261-280

[3] Radical cyclisation onto imidazoles and benzimidazoles [J].

Aldabbagh, F ;

Bowman, WR .

TETRAHEDRON, 1999, 55 (13) :4109-4122

[4] Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH [J].

Aldabbagh, F ;

Bowman, WR ;

Mann, E .

TETRAHEDRON LETTERS, 1997, 38 (45) :7937-7940

[5] Radical cyclisation onto imidazoles and benzimidazoles [J].

Aldabbagh, F ;

Bowman, WR .

TETRAHEDRON LETTERS, 1997, 38 (21) :3793-3794

[6]

ALLIN SA, 2002, IN PRESS TETRAHEDRON

[7] Acyl radical cyclisation onto pyrroles [J].

Allin, SM ;

Barton, WRS ;

Bowman, WR ;

McInally, T .

TETRAHEDRON LETTERS, 2001, 42 (44) :7887-7890

[8] OXIDATIVE RADICAL CYCLIZATION TO PYRROLES UNDER REDUCING CONDITIONS - REDUCTIVE DESULFONYLATION OF ALPHA-SULFONYLPYRROLES WITH TRI-N-BUTYLTIN HYDRIDE [J].

ANTONIO, Y ;

DELACRUZ, ME ;

GALEAZZI, E ;

GUZMAN, A ;

BRAY, BL ;

GREENHOUSE, R ;

KURZ, LJ ;

LUSTIG, DA ;

MADDOX, ML ;

MUCHOWSKI, JM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01) :15-22

[9] RADICAL DECARBOXYLATIVE ADDITION ONTO PROTONATED HETEROAROMATIC (AND RELATED) COMPOUNDS [J].

BARTON, DHR ;

GARCIA, B ;

TOGO, H ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1986, 27 (12) :1327-1330

[10] New cascade 2-indolylacyl radical addition-cyclization reactions [J].

Bennasar, ML ;

Roca, T ;

Griera, R ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7547-7551

← 1 2 3 →