Butenolide annelation using a manganese(III) oxidation.: A synthesis of 4-arylfuran-2(5H)-ones

被引：26

作者：

Demir, AS ^{[1
]}

Camkerten, N ^{[1
]}

Gercek, Z ^{[1
]}

Duygu, N ^{[1
]}

Reis, O ^{[1
]}

Arikan, E ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON | 1999年 / 55卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(99)00036-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure was developed for the annelation of a butenolide to an aromatic ketone that highlighted a manganese(III) oxidation of aromatic ketones. The oxidation of aromatic ketones with manganese(III) acetate in the presence of 2;bromoacetic acid or the Mn(II) salt of this carboxylic acid provided a regioselectively convenient synthesis of 2-(2-bromoacetoxy) ketones. An Arbuzov or Wittig reaction of 2-(2-bromoacetoxy) ketones followed by cyclisation furnished 4-arylfuran-2(5H)-ones in good yield. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：2441 / 2448

页数：8

共 33 条

[1]

ARNDT D, 1981, MANGANESE COMPOUNDS, pCH1

[2]

BAUER G, 1962, HDB PRAEPARATIVEN AN, P1283

[3] ANALOGS OF GAMMA-HYDROXYBUTYRIC ACID - SYNTHESIS AND BINDING-STUDIES [J].

BOURGUIGNON, JJ ;

SCHOENFELDER, A ;

SCHMITT, M ;

WERMUTH, CG ;

HECHLER, V ;

CHARLIER, B ;

MAITRE, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (05) :893-897

[4] SYNTHESIS OF BUTENOLIDES FROM ALPHA-(PHENYLTHIO)-KETONES AND ALPHA-(PHENYTHIO)-ESTERS - CRYSTAL-STRUCTURE OF AN INTERMEDIATE BETA-PHENYLTHIO-GAMMA-LACTONE [J].

BROWNBRIDGE, P ;

EGERT, E ;

HUNT, PG ;

KENNARD, O ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (10) :2751-2759

[5] STUDIES ON NUCLEOPHILIC RING-OPENING OF SOME EPOXIDES IN POLAR PROTIC SOLVENTS .1. [J].

CHATTERJEE, A ;

BANERJEE, D ;

MALLIK, R .

TETRAHEDRON, 1977, 33 (01) :85-94

[6]

CHRETIEN A, 1936, B SOC CHIM FR, V3, P2385

[7]

CIATTINI PG, 1986, SYNTHESIS-STUTTGART, P70

[8]

COREY EJ, 1960, J AM CHEM SOC, V82, P918

[9] Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones [J].

Demir, AS ;

Hamamci, H ;

Tanyeli, C ;

Akhmedov, IM ;

Doganel, F .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1673-1677

[10] SYNTHESIS OF ALPHA'-ACYLOXY ENONES FROM ENONES USING MANGANESE(III) ACETATE IN COMBINATION WITH MANGANESE(II) CARBOXYLATES OR CARBOXYLIC-ACIDS [J].

DEMIR, AS ;

JEGANATHAN, A ;

WATT, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4020-4022

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