A single-step synthesis of symmetrical 1,3-diarylisobenzofurans

被引:14
作者
Benderradj, Farah [1 ]
Nechab, Malek [1 ]
Einhorn, Cathy [1 ]
Einhorn, Jacques [1 ]
机构
[1] Univ Grenoble 1, UMR 5616, Etud Dynam & Struct Select Lab, F-38041 Grenoble 9, France
关键词
Grignard reactions; Diels-Alder reactions; fused-ring systems; heterocycles; nucleophilic addition;
D O I
10.1055/s-2006-948179
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient single-step synthesis of various symmetrically substituted 1,3-diarylisobenzofurans from readily available 3-methoxy-3H-isobenzofuran-1-one (1 a) and two equivalents of aryl Grignard reagents is described. The title compounds are obtained in medium to high isolated yields. Crude isobenzofuran has also been trapped by maleimide, furnishing pure Diels-Alder adduct almost quantitatively.
引用
收藏
页码:2035 / 2038
页数:4
相关论文
共 22 条
[1]   Absorption and fluorescence spectra of certain dihydroisobenzofurans and isobenzofurans [J].
Adams, R ;
Gold, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :2038-2042
[2]   Diene addition products to diaroylethylenes and their transformation products II [J].
Adams, R ;
Wearn, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1233-1237
[3]  
ALHAMDANY R, 1989, J CHEM RES-S, P82
[4]   THIOPHENES .7. SYNTHESIS AND CHARACTERIZATION OF NEW ANNELATED TERHETEROCYCLES [J].
BAUERLE, P ;
GOTZ, G ;
EMERLE, P ;
PORT, H .
ADVANCED MATERIALS, 1992, 4 (09) :564-568
[5]   The action of sulfuric acid on diarylphthalins. II. Mechanism of the reaction [J].
Blicke, FF ;
Patelski, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :559-562
[6]  
CANONNE P, 1988, TETRAHEDRON, V44, P2903
[7]   CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .26. BENZOCYCLOBUTADIENOQUINONE - SYNTHESIS AND SIMPLE TRANSFORMATIONS [J].
CAVA, MP ;
POHL, RJ ;
NAPIER, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2076-&
[8]  
COURTOT P, 1965, B SOC CHIM FR, P2259
[9]   SYNTHESIS OF PILOQUINONE, A METABOLITE OF STREPTOMYCES-PILOSUS ETTLINGER [J].
CRESP, TM ;
GILES, RGF ;
SARGENT, MV ;
BROWN, C ;
SMITH, DO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (21) :2435-2447
[10]  
Einhorn C, 2001, ANGEW CHEM INT EDIT, V40, P1926, DOI 10.1002/1521-3773(20010518)40:10<1926::AID-ANIE1926>3.0.CO