New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins

被引：104

作者：

Biagetti, M ^{[1
]}

Bellina, F ^{[1
]}

Carpita, A ^{[1
]}

Stabile, P ^{[1
]}

Rossi, R ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 25期

关键词：

iodine heterocycles; pyrones; isocoumarins; Stille coupling; palladium catalysis;

D O I：

10.1016/S0040-4020(02)00469-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Iodo-2(2H)-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH2Cl2 or C6H6 at 20degreesC (Method C) or by treatment of these esters with ICl in CH2Cl2 at 20degreesC (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2H)-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5023 / 5038

页数：16

共 59 条

[1]

[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23

[2] REGIOSELECTIVITY IN THE REDUCTIVE CLEAVAGE OF PYROGALLOL DERIVATIVES - REDUCTIVE ELECTROPHILIC SUBSTITUTION OF ACETALS OF 2,3-DIMETHOXYPHENOL [J].

AZZENA, U ;

MELLONI, G ;

PISANO, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (03) :261-266

[3] On the stereoselection of iodolactonizations of 3-silyloxyalk-5-enoic acids [J].

Bedford, SB ;

Fenton, G ;

Knight, DW ;

Shaw, DE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (13) :1505-1509

[4] Total synthesis of rubrolide M and some of its unnatural congeners [J].

Bellina, F ;

Anselmi, C ;

Rossi, R .

TETRAHEDRON LETTERS, 2002, 43 (11) :2023-2027

[5] A novel route to 6-substituted and 5,6-disubstituted 2-pyrones [J].

Bellina, F ;

Biagetti, M ;

Carpita, A ;

Rossi, R .

TETRAHEDRON LETTERS, 2001, 42 (15) :2859-2863

[6] Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions [J].

Bellina, F ;

Anselmi, C ;

Rossi, R .

TETRAHEDRON LETTERS, 2001, 42 (23) :3851-3854

[7] 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

[8] 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

[9]

Biagetti M, 2002, EUR J ORG CHEM, V2002, P1063, DOI 10.1002/1099-0690(200203)2002:6<1063::AID-EJOC1063>3.0.CO

[10]

2-M

← 1 2 3 4 5 6 →