A general and efficient PIFA mediated synthesis of heterocycle-fused quinolinone derivatives

被引：51

作者：

Herrero, MT ^{[1
]}

Tellitu, I ^{[1
]}

Domínguez, E ^{[1
]}

Hernández, S ^{[1
]}

Moreno, I ^{[1
]}

SanMartín, R ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2002年 / 58卷 / 42期

关键词：

hypervalent iodine; heterocycles; cyclizations; biaryl coupling; quinolinones;

D O I：

10.1016/S0040-4020(02)00903-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new application of the hypervalent iodine reagent phenyliodine(III)bis(trifluoroacetate) (PEFA) has been developed for the construction of a series of N, O, S-containing heterocycle-fused quinolinone derivatives in a general and efficient way. An alternative approach to the formation of these novel tricyclic heterocycles by a PIFA mediated aryl-heteroaryl coupling reaction is also presented. (C) 2002 Elsevier Science Ltd. All lights reserved.

引用

页码：8581 / 8589

页数：9

共 62 条

[1]

[Anonymous], COMPREHENSIVE HETERO

[2] Hypervalent iodine(III)-induced intramolecular cyclization of α-(aryl)alkyl-β-dicarbonyl compounds:: A convenient synthesis of benzannulated and spirobenzannulated compounds [J].

Arisawa, M ;

Ramesh, NG ;

Nakajima, M ;

Tohma, H ;

Kita, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :59-65

[3]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[4] A NOVEL ELECTROPHILIC N-AMIDATION VIA ELECTRON DEFICIENT COMPLEXES - ACTION OF FERRIC-CHLORIDE ON N-ACETYLOXYAMIDES [J].

CHEREST, M ;

LUSINCHI, X .

TETRAHEDRON LETTERS, 1989, 30 (06) :715-718

[5] Direct conversion of carboxylic esters into ketones using organoaluminum complexes [J].

Chung, EA ;

Cho, CW ;

Ahn, KH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7590-7591

[6] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - SYNTHESIS OF (+/-)-SEPTICINE AND (+/-)-TYLOPHORINE [J].

COMINS, DL ;

MORGAN, LA .

TETRAHEDRON LETTERS, 1991, 32 (42) :5919-5922

[7]

COMINS DL, 1997, PROGR HETEROCYCLIC C, V9, P231

[8] Structure-activity relationships in a series of 2(1H)-quinolones bearing different acidic function in the 3-position: 6,7-Dichloro-2(1H)-oxoquinoline-3-phosphonic acid, a new potent and selective AMPA/kainate antagonist with neuroprotective properties [J].

Desos, P ;

Lepagnol, JM ;

Morain, P ;

Lestage, P ;

Cordi, AA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) :197-206

[9] A convenient one-pot preparative method for 4,5-diarylisoxazoles involving amine exchange reactions [J].

Dominguez, E ;

Ibeas, E ;

deMarigorta, EM ;

Palacios, JK ;

SanMartin, R .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5435-5439

[10]

Hantzsch A, 1887, CHEM BER, V20, P3118, DOI [10.1002/cber.188702002200, DOI 10.1002/CBER.188702002200]

← 1 2 3 4 5 6 7 →