Synthesis of isocoumarins and α-pyrones via electrophilic cyclization

被引：346

作者：

Yao, TL ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 15期

关键词：

D O I：

10.1021/jo034308v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.

引用

页码：5936 / 5942

页数：7

共 64 条

[1] FUSALANIPYRONE, A MONOTERPENOID FROM FUSARIUM-SOLANI [J].

ABRAHAM, WR ;

ARFMANN, HA .

PHYTOCHEMISTRY, 1988, 27 (10) :3310-3311

[2] GIBEPYRONES - ALPHA-PYRONES FROM GIBBERELLA-FUJIKUROI [J].

BARRERO, AF ;

OLTRA, JE ;

HERRADOR, MM ;

CABRERA, E ;

SANCHEZ, JF ;

QUILEZ, JF ;

ROJAS, FJ ;

REYES, JF .

TETRAHEDRON, 1993, 49 (01) :141-150

[3] ISOCOUMARINS - DEVELOPMENTS SINCE 1950 [J].

BARRY, RD .

CHEMICAL REVIEWS, 1964, 64 (03) :229-+

[4] SYNTHESIS OF NATURAL ISOCOUMARINS, ARTEMIDIN AND 3-PROPYLISOCOUMARIN [J].

BATU, G ;

STEVENSON, R .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1532-1534

[5] Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids [J].

Bellina, F ;

Biagetti, M ;

Carpita, A ;

Rossi, R .

TETRAHEDRON, 2001, 57 (14) :2857-2870

[6] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].

Bellina, F ;

Ciucci, D ;

Vergamini, P ;

Rossi, R .

TETRAHEDRON, 2000, 56 (16) :2533-2545

[7] New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins [J].

Biagetti, M ;

Bellina, F ;

Carpita, A ;

Stabile, P ;

Rossi, R .

TETRAHEDRON, 2002, 58 (25) :5023-5038

[8] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[9]

CAMPBELL IB, 1994, SONOGASHIRA CU PD CA, P217

[10] 3-aryl and 5-aryl-4-methoxy-6-methyl-2H-pyran-2-ones by Suzuki cross-coupling reactions of 3- and 5-halogeno-4-methoxy-6-methyl-2H-pyran-2-ones [J].

Cerezo, S ;

Moreno-Mañas, M ;

Pleixats, R .

TETRAHEDRON, 1998, 54 (27) :7813-7818

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