Novel applications of hypervalent iodine:: PIFA mediated synthesis of benzo[c]phenanthiridines and benzo[c]phenanthridinones

被引：73

作者：

Moreno, I ^{[1
]}

Tellitu, I ^{[1
]}

Etayo, J ^{[1
]}

SanMartín, R ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 25期

关键词：

hypervalent iodine; PIFA; biaryl coupling; benzo[c]phenanthridines; benzo[c]phenanthridinones;

D O I：

10.1016/S0040-4020(01)00459-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient access to benzo[c]phenanthridines and phenanthridinones is achieved by the action of phenyliodine(m)-bis(trifluoroacetate) (PIFA) on properly substituted benzylnaphthylamines and naphthylbenzamides, respectively. This reagent promotes a non-phenolic oxidative biaryl coupling process, the key step of the synthesis. A study of the electronic and steric requirements of the substrates is carried out since, in some cases, dimerization processes prevail over intramolecular cyclization. A mechanistic proposal is also included. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5403 / 5411

页数：9

共 49 条

[11]

Dostál J, 2000, CHEM LISTY, V94, P15

[12] SEQUENTIAL ALKOXY RADICAL FRAGMENTATION-TRANSANNULAR RADICAL CYCLIZATION-RADICAL RING EXPANSION REACTIONS - A NEW APPROACH TO BICYCLO[5.3.0]DECANONES AND TO BICYCLO[6.3.0]UNDECANONES [J].

ELLWOOD, CW ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1991, 32 (12) :1591-1594

[13] Synthesis of phenanthridones, quinolinequinones and 7-azasteroids [J].

González, C ;

Guitián, E ;

Castedo, L .

TETRAHEDRON, 1999, 55 (16) :5195-5206

[14]

ISHII H, 1983, CHEM PHARM BULL, V31, P3039

[15] SYNTHESIS OF MACARPINE AND ITS CYTOTOXICITY - TOWARD A SYNTHETIC ROUTE FOR 12-ALKOXYBENZO[C]PHENANTHRIDINE ALKALOIDS THROUGH AROMATIC NITROSATION UNDER BASIC CONDITION [J].

ISHIKAWA, T ;

SAITO, T ;

ISHII, H .

TETRAHEDRON, 1995, 51 (31) :8447-8458

[16] A FORMAL NEW ACCESS TO THE BENZO[C]PHENANTHRIDINE ALKALOIDS, SYNTHESIS OF NITIDINE AND O-METHYL FAGARONINE ANALOGS [J].

JANIN, YL ;

BISAGNI, E .

TETRAHEDRON, 1993, 49 (45) :10305-10316

[17]

KESSAR S V, 1977, Tetrahedron Letters, V17, P1459

[18] A NOVEL OXIDATIVE AZIDATION OF AROMATIC-COMPOUNDS WITH HYPERVALENT IODINE REAGENT, PHENYLIODINE(III) BIS(TRIFLUOROACETATE) (PIFA) AND TRIMETHYLSILYL AZIDE [J].

KITA, Y ;

TOHMA, H ;

INAGAKI, M ;

HATANAKA, K ;

YAKURA, T .

TETRAHEDRON LETTERS, 1991, 32 (34) :4321-4324

[19]

Kita Y, 1999, CHEM PHARM BULL, V47, P241

[20] Hypervalent iodine(III) induced intramolecular cyclization of substituted phenol ethers bearing an alkyl azido sidechain - A novel synthesis of quinone imine ketals [J].

Kita, Y ;

Egi, M ;

Okajima, A ;

Ohtsubo, M ;

Takada, T ;

Tohma, H .

CHEMICAL COMMUNICATIONS, 1996, (13) :1491-1492

← 1 2 3 4 5 →