Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

被引：63

作者：

Aldabbagh, F ^{[1
]}

Bowman, WR ^{[1
]}

Mann, E ^{[1
]}

Slawin, AMZ ^{[1
]}

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(99)00419-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：8111 / 8128

页数：18

共 58 条

[1] SRN1 AND OXIDATIVE ADDITION-REACTIONS OF NITROIMIDAZOLE ANIONS [J].

ADEBAYO, ATOM ;

BOWMAN, WR ;

SALT, WG .

TETRAHEDRON LETTERS, 1986, 27 (17) :1943-1946

[2] RADICAL-NUCLEOPHILIC SUBSTITUTION (SRN1) REACTIONS .5. ANIONS OF NITROIMIDAZOLES IN SRN1 AND OXIDATIVE ADDITION-REACTIONS [J].

ADEBAYO, ATOM ;

BOWMAN, WR ;

SALT, WG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2819-2827

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

Aldabbagh, F ;

Bowman, WR .

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

[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] DECARBONYLATION REACTION OF IMIDAZOLE-2-CARBALDEHYDES IN ETHANOL [J].

ANTONINI, I ;

CRISTALLI, G ;

FRANCHETTI, P ;

GRIFANTINI, M ;

GULINI, U ;

MARTELLI, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (07) :1201-1203

[7] 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

[8] INTRAMOLECULAR SH2' MACROCYCLIZATIONS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

MITCHELL, MB ;

ROBERTSON, J .

TETRAHEDRON, 1991, 47 (30) :5901-5918

[9] TANDEM RADICAL TRANSLOCATION AND HOMOLYTIC AROMATIC-SUBSTITUTION - A CONVENIENT AND EFFICIENT ROUTE TO OXINDOLES [J].

BECKWITH, ALJ ;

STOREY, JMD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (09) :977-978

[10] INTRAMOLECULAR AROMATIC-SUBSTITUTION (SRN1) REACTIONS - USE OF ENTRAINMENT FOR THE PREPARATION OF BENZOTHIAZOLES [J].

BOWMAN, WR ;

HEANEY, H ;

SMITH, PHG .

TETRAHEDRON LETTERS, 1982, 23 (48) :5093-5096

← 1 2 3 4 5 6 →