Furan-fused 3-sulfolene as a novel building block: Intermolecular Diels-Alder reactions of 4H,6H-thieno[3,4-c]furan 5,5-dioxide

被引:10
作者
Suzuki, T [1 ]
Kubomura, K [1 ]
Takayama, H [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 03期
关键词
D O I
10.1039/a604600b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A furan-fused 3-sulfolene 4N,6H-thieno[3,4-c]furan 5,5-dioxide 1, can be used as a bis-diene, reacting sequentially with a variety of dienophiles to construct four types of skeleton, depending on the dienophile and the reaction conditions. The 3-sulfolene moiety of the furansulfolene not only functions as the s-cis-diene part in Diels-Alder reactions, but also extends the range of the Diels-Alder reactions of the furan moiety with various dienophiles through its desulfonylation to form the s-cis-diene.
引用
收藏
页码:251 / 256
页数:6
相关论文
共 23 条
[1]   ALKYLATION OF 4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE AND ITS USE AS A 3,4-DIMETHYLENEFURAN SYNTHON IN INTRAMOLECULAR DIELS-ALDER REACTIONS [J].
ANDO, K ;
AKADEGAWA, N ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) :1765-1767
[2]   ALKYLATION OF 4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE AND ITS USE AS A 3,4-DIMETHYLENEFURAN SYNTHON IN INTRAMOLECULAR DIELS-ALDER REACTION [J].
ANDO, K ;
AKADEGAWA, N ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2263-2268
[3]   NOVEL FORMATION OF DIENES WITH GREATER STERIC CONGESTION RESULTING FROM THE DIELS-ALDER REACTION DESULFONYLATION SEQUENCE OF 4-ACYL-4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDES [J].
ANDO, K ;
HATANO, C ;
AKADEGAWA, N ;
SHIGIHARA, A ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (12) :870-873
[4]   ORGANIC REACTIONS AT HIGH-PRESSURE - CYCLOADDITIONS WITH FURANS [J].
DAUBEN, WG ;
KRABBENHOFT, HO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) :1992-1993
[5]   DIELS-ALDER REACTION OF FURAN WITH SOME DIENOPHILES [J].
EGGELTE, TA ;
KONING, HD ;
HUISMAN, HO .
TETRAHEDRON, 1973, 29 (16) :2491-2493
[6]   A NOVEL-APPROACH TO FUNCTIONALIZED POLYCYCLIC SYSTEMS - INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-ACYLATED DERIVATIVES OF 4H,6H-THIENO[3,4-C]FURAN 5,5-DIOXIDE [J].
HAYASHI, T ;
KAWAKAMI, Y ;
KONNO, K ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (20) :2387-2388
[7]  
JOLIVET J, 1960, LIEBIGS ANN CHEM, P1165
[8]   ORGANIC SYNTHESES UNDER HIGH-PRESSURE .6. [2+4]-CYCLOADDITIONS UNDER HIGH-PRESSURE - 1ST REALIZATION OF A DIELS-ALDER ADDITION OF FURAN WITH SIMPLE 1,4-BENZOQUINONES [J].
JURCZAK, J ;
KOZLUK, T ;
FILIPEK, S ;
EUGSTER, CH .
HELVETICA CHIMICA ACTA, 1983, 66 (01) :222-225
[9]   NOVEL-APPROACH TO FUNCTIONALIZED POLYCYCLIC SYSTEMS - LEWIS-ACID INDUCED REARRANGEMENTS OF 7-OXA-2,3-DIMETHYLENENORBORNENE DERIVATIVES [J].
KONNO, K ;
MAKI, S ;
SAGARA, S ;
TAKAYAMA, H .
TETRAHEDRON LETTERS, 1995, 36 (11) :1865-1866
[10]   HIGH-PRESSURE ORGANIC-CHEMISTRY .5. DIELS-ALDER REACTIONS OF FURAN WITH ACRYLIC AND MALEIC ESTERS [J].
KOTSUKI, H ;
NISHIZAWA, H ;
OCHI, M ;
MATSUOKA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (02) :496-499