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Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2021-09-16 , DOI: 10.3762/bjoc.17.159
Ren-Jie Fang 1 , Chen Yan 1 , Jing Sun 1 , Ying Han 1 , Chao-Guo Yan 1
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The p-TsOH-catalyzed Diels–Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 °C afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones or benzylideneacetone in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their acid-catalyzed Diels–Alder reaction and sequential aromatization process.

中文翻译:

通过多米诺狄尔斯-阿尔德反应高效合成多官能化咔唑和吡咯并[3,4-c]咔唑

p的3-(吲哚-3-基)-TsOH催化狄尔斯-阿尔德反应,在60与在甲苯中的查耳酮马来酰亚胺℃下得到的四氢吡咯并2个非对映体[3,4 -c ]咔唑,其可通过DDQ氧化脱氢室温下在乙腈中以高产率得到芳构化的吡咯并[3,4 -c ]咔唑。另一方面,3-(indol-3-yl)-1,3-diphenylpropan-1-ones 与查耳酮或亚苄基丙酮在乙腈中在p存在下的一锅反应-TsOH 和 DDQ 产生了令人满意的多官能化咔唑。反应机理包括 3-(indol-3-yl)-1,3-diphenylpropan-1-ones 的 DDQ 氧化脱氢为相应的 3-vinylindoles,它们的酸催化 Diels-Alder 反应和顺序芳构化过程。
更新日期:2021-09-16
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