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

被引:21
作者
ANDO, K [1 ]
AKADEGAWA, N [1 ]
TAKAYAMA, H [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
关键词
D O I
10.1039/c39910001765
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
4H,6H-thieno[3,4-c]furan 5,5-dioxide 1 was readily converted to the 4-alkylated compounds 2 and the appropriate compounds 2 were submitted to intramolecular Diels-Alder reactions to afford fused furans 8a and b in good yields.
引用
收藏
页码:1765 / 1767
页数:3
相关论文
共 11 条
[1]  
MANCUSO AJ, 1981, SYNTHESIS-STUTTGART, P165
[2]   INVESTIGATIONS INTO A MILD DIELS-ALDER APPROACH TO 6-SUBSTITUTED QUINAZOLINE-2,4-DIONE DERIVATIVES [J].
MCNALLY, JJ ;
PRESS, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :245-251
[3]   IMPROVED SYNTHESIS OF 3,4-DISUBSTITUTED FURANS - USE OF PHASE-TRANSFER CONDITIONS [J].
PRICE, ME ;
SCHORE, NE .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2777-2778
[4]   HETEROCYCLIC AROMATIC NON-KEKULE MOLECULES - SYNTHESIS AND SOLUTION-PHASE CHEMISTRY OF THE SINGLET BIRADICALS 3,4-DIMETHYLENEFURAN AND 3,4-DIMETHYLENETHIOPHENE [J].
STONE, KJ ;
GREENBERG, MM ;
BLACKSTOCK, SC ;
BERSON, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (10) :3659-3671
[5]   NOVEL BUILDING BLOCK, FURAN-ANNELATED 3-SULPHOLENE - DIELS-ALDER REACTIONS OF 4,6-DIHYDROTHIENO[3,4-C]FURAN S,S-DIOXIDE [J].
SUZUKI, T ;
KUBOMURA, K ;
FUCHII, H ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (23) :1687-1689
[6]   NOVEL, READILY OCCURRING, AND STEREOSELECTIVE SYNTHESIS OF CONJUGATED TRIENES USING 2-TRIALKYLSTANNYL-2,5-DIHYDROTHIOPHENE S,S-DIOXIDES [J].
TAKAYAMA, H ;
SUZUKI, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (15) :1044-1045
[7]  
UMBERT MA, 1977, J AM CHEM SOC, V96, P5526
[8]   STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA-HYDROXY-1,3-DIENES VIA THE REACTION OF 2,5-DIHYDROTHIOPHENE S,S-DIOXIDES WITH CARBONYL-COMPOUNDS [J].
YAMADA, S ;
SUZUKI, H ;
NAITO, H ;
NOMOTO, T ;
TAKAYAMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) :332-333
[9]   STEREOSELECTIVE SYNTHESIS OF (E)-CONJUGATED, (E,Z)-CONJUGATED, AND (E,E)-CONJUGATED DIENES VIA ALKYLATION OF 3-SULFOLENES AS THE KEY STEP [J].
YAMADA, S ;
OHSAWA, H ;
SUZUKI, T ;
TAKAYAMA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4934-4940
[10]  
YAMAGUCHI Y, 1990, HETEROCYCLES, V30, P223