NEW BUILDING-BLOCKS, 3,5-DIHYDRO-1H-THIENO[3,4-C]PYRROLE 2,2-DIOXIDES - PREPARATION AND THEIR DIELS-ALDER REACTION WITH DIMETHYL ACETYLENEDICARBOXYLATE

被引:31
作者
ANDO, K [1 ]
KANKAKE, M [1 ]
SUZUKI, T [1 ]
TAKAYAMA, H [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
关键词
D O I
10.1016/0040-4020(94)00968-Z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 3, have been prepared by the oxidation of their corresponding pyrroline derivatives 4 with DDQ or Chemical MnO2. The Diels-Alder reaction of 3 with dimethyl acetylenedicarboxylate gave new types of compounds: 7aza-2,3-dimethylenenorbornenes A, the 1:2 adducts B, 1a,3a,6,9-tetrahydrobenz[g]indoles C, and dihydroindolosulfolene D depending on the reaction conditions and the N-substituents. The reaction of 3 with bis(tert-butylsulfonyl)acetylene was also described.
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页码:129 / 138
页数:10
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