Intramolecular [4+2] cycloaddition reactions of ketenimines:: A new synthesis of benz[b]acridines

被引：21

作者：

Alajarín, M ^{[1
]}

Vidal, A ^{[1
]}

Ortín, MM ^{[1
]}

Tovar, F ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, Murcia, Spain

来源：

SYNTHESIS-STUTTGART | 2002年 / 16期

关键词：

azides; acridines; cycloadditions; polycycles; ketenimines; phosphazenes;

D O I：

10.1055/s-2002-35234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-[2-(2-Propenyl)phenyl]-C,C-diphenyl ketenimines undergo a thermally induced intramolecular [4 + 2] cycloaddition to give 5,11,11 a, 12-tetrahydrobenz[b]acridines, which are converted into the fully aromatic benz[b]acridines by oxidation with Pd/C in refluxing ortho-xylene.

引用

页码：2393 / 2398

页数：6

共 21 条

[1] Formal [4+2] intramolecular cycloaddition ketenimine-imine.: Synthesis of benzimidazo[1,2-b]isoquinolines [J].

Alajarín, M ;

Vidal, A ;

Tovar, F ;

Conesa, C .

TETRAHEDRON LETTERS, 1999, 40 (33) :6127-6130

[2] Periselective intramolecular [4+2] cycloadditions of ketenimines:: synthesis of pyrido[1,2-a]benzimidazoles [J].

Alajarín, M ;

Vidal, A ;

Tovar, F .

TETRAHEDRON LETTERS, 2000, 41 (36) :7029-7032

[3]

ALAJARIN M, 2000, TARGETS HETEROCYCL S, V4, P293

[4]

ALKHADER MA, 1980, SYNTHESIS-STUTTGART, P381

[5] SYNTHESIS OF BENZ[B]ACRIDINE-6,11,12-TRIONES [J].

ALVAREZ, M ;

AJANA, W ;

LOPEZCALAHORRA, F ;

JOULE, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :917-919

[6]

BARKER MW, 1980, CHEM KETENES ALLENES, P701

[7] A SIMPLE SYNTHESIS OF AAPTAMINE, A 1H-BENZO[DE][1,6]-NAPHTHYRIDINE ALKALOID [J].

BASSOLI, A ;

MADDINELLI, G ;

RINDONE, B ;

TOLLARI, S ;

CHIOCCARA, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :150-151

[8] Manganese(III) acetate initiated oxidative free radical reaction between 1,4-naphthoquinones and ethyl nitroacetate [J].

Chuang, CP ;

Wu, YL ;

Jiang, MC .

TETRAHEDRON, 1999, 55 (37) :11229-11236

[9] RECENT ADVANCES IN THE STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

KASUKHIN, LF .

TETRAHEDRON, 1992, 48 (08) :1353-1406

[10] 60 YEARS OF STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

ZHMUROVA, IN ;

KASUKHIN, LF .

TETRAHEDRON, 1981, 37 (03) :437-472

← 1 2 3 →