Nucleophilic substitution of hydrogen in heterocyclic chemistry

被引：365

作者：

Makosza, M ^{[1
]}

Wojciechowski, K ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

来源：

CHEMICAL REVIEWS | 2004年 / 104卷 / 05期

关键词：

D O I：

10.1021/cr020086+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophiles can react with electron-deficient arenes in a variety of ways. The most important of them is addition to the ring to form anionic σ-adducts. This review covers early examples of reactions that proceed via addition of nucleophiles to electron-deficient arenes in positions occupied with hydrogen followed by transformations of the formed σH-adducts.

引用

页码：2631 / 2666

页数：36

共 352 条

[11] Selective vicarious nucleophilic amination of 3-nitropyridines [J].

Bakke, JM ;

Svensen, H ;

Trevisan, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04) :376-378

[12] The reaction of 3-nitropyridine with sulfite ions; a pathway to 2,5-disubstituted pyridines [J].

Bakke, JM ;

Ranes, E ;

Romming, C ;

Sletvold, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (08) :1241-1243

[13] The oxidative amination of 3-nitropyridines [J].

Bakke, JM ;

Svensen, H .

TETRAHEDRON LETTERS, 2001, 42 (26) :4393-4395

[14] ALKYLATION ORIENTATION RULES IN CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO NITROPYRROLE AND NITROTHIOPHENE SYSTEMS [J].

BALLINI, R ;

BARTOLI, G ;

BOSCO, M ;

DALPOZZO, R ;

MARCANTONI, E .

TETRAHEDRON, 1988, 44 (20) :6435-6440

[15] NOVEL NUCLEOPHILE-DEPENDENT CINE-SUBSTITUTION IN ALPHA-NITROFURANS [J].

BARNES, BJ ;

NEWCOMBE, PJ ;

NORRIS, RK ;

WILSON, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1408-1409

[16] THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES [J].

BARTOLI, G ;

PALMIERI, G ;

BOSCO, M ;

DALPOZZO, R .

TETRAHEDRON LETTERS, 1989, 30 (16) :2129-2132

[17] CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO PARA-NITROTOLUENE - COMPETITIVE ATTACK OF ENTERING ALKYL GROUP TO ORTHO AND PARA POSITIONS [J].

BARTOLI, G ;

BOSCO, M ;

PEZZI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2932-2933

[18] REACTIONS OF NITROBENZOTHIAZOLES WITH GRIGNARD-REAGENTS - ORIENTATION OF ALKYLATION WITH RESPECT TO NITRO-GROUP POSITION [J].

BARTOLI, G ;

LEARDINI, R ;

LELLI, M ;

ROSINI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :884-887

[19]

BARTOLI G, 1976, SYNTHESIS-STUTTGART, P270

[20] REACTIONS OF NITROARENES WITH GRIGNARD-REAGENTS - GENERAL METHOD OF SYNTHESIS OF ALKYL-NITROSO-SUBSTITUTED BICYCLIC AROMATIC SYSTEMS [J].

BARTOLI, G ;

LEARDINI, R ;

MEDICI, A ;

ROSINI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (07) :692-696

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