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Iodine promoted annulation reaction for selective construction of Spiro[indene-2,1′-pyrido[4,3-b]indole] and Benzo[5,6]pyrrolo[3′,2': 3,4]cyclohepta[1,2-b]indole
Tetrahedron ( IF 2.1 ) Pub Date : 2024-05-09 , DOI: 10.1016/j.tet.2024.134026
Ling-Yun Zhu , Jing Sun , Dan Liu , Chao-Guo Yan

I promoted cycloaddition reaction of 2-hydroxy-2-(indol-3-yl)-indane-1,3-diones with the generated -enamino esters, which were generated from the reaction of arylamines and dialkyl but-2-ynedioates, showed very interesting molecular diversity. In the presence of 30 % mmol iodine, the reaction in acetonitrile at 80 °C resulted in the novel spiro [indene-2,1′-pyrido [4,3-]indole] derivatives in good yields. On the other hand, in the presence of 80 % mmol iodine, the reaction in acetonitrile at 60 °C gave the ring-expanded benzo [5,6]pyrrolo [3′,2':3,4]cyclohepta [1,2-]indole derivatives in moderate to good yields. Additionally, the similar iodine-promoted reaction of 2-(indol-2-yl)diarylmethanols and -enamino esters gave the unique 1,1,2-triphenyl-2,9-dihydropyrido [3,4-]indoles in satisfactory yields. A plausible domino annulation mechanism was rationally proposed for the formation of various polycyclic compounds.

中文翻译:


碘促进环化反应选择性构建螺[茚-2,1'-吡啶并[4,3-b]吲哚]和苯并[5,6]吡咯并[3',2': 3,4]环庚[1, 2-b]吲哚



我促进了2-羟基-2-(吲哚-3-基)-茚满-1,3-二酮与生成的烯氨基酯的环加成反应,烯氨基酯是由芳基胺和丁-2-炔二酸二烷基酯反应生成的,表明非常有趣的分子多样性。在 30% mmol 碘存在下,在 80°C 的乙腈中进行反应,以良好的收率生成新型螺[茚-2,1'-吡啶并[4,3-]吲哚]衍生物。另一方面,在 80% mmol 碘存在下,在乙腈中于 60°C 反应,得到扩环苯并[5,6]吡咯并[3',2':3,4]环庚[1,2 -]吲哚衍生物,产率中等至良好。此外,类似的碘促进的2-(吲哚-2-基)二芳基甲醇和烯氨基酯的反应以令人满意的收率得到了独特的1,1,2-三苯基-2,9-二氢吡啶并[3,4-]吲哚。合理地提出了一种合理的多米诺环化机制来形成各种多环化合物。
更新日期:2024-05-09
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