Synthesis of 7'-Arylidenespiro[indoline-3,1'-pyrrolizines] and 7'-Arylidenespiro[indene-2,1'-pyrrolizines] via [3 + 2] Cycloaddition and β-C-H Functionalized Pyrrolidine.,The Journal of Organic Chemistry

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Synthesis of 7'-Arylidenespiro[indoline-3,1'-pyrrolizines] and 7'-Arylidenespiro[indene-2,1'-pyrrolizines] via [3 + 2] Cycloaddition and β-C-H Functionalized Pyrrolidine.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-09-19 , DOI: 10.1021/acs.joc.9b01920
Ying Huang _{1,

2} , Hui-Lin Fang ₁ , Yi-Xin Huang ₂ , Jing Sun ₁ , Chao-Guo Yan ₁

Affiliation

The acetic acid catalyzed three-component reaction of pyrrolidine, aromatic aldehydes, and 3-arylideneoxindolin-2-ones in refluxing toluene afforded functionalized 7'-arylidenespiro[indoline-3,1'-pyrrolizines] in good yields and with high diastereoselectivity. The similar three-component reaction with 2-arylidene-1,3-indanediones also gave 7'-arylidenespiro[indene-2,1'-pyrrolizines] in good yields. However, the reaction with 3-phenacylideneoxindoles resulted in a mixture of spiro[indoline-3,1'-pyrrolizines] and 7'-arylidene-substituted spirooxindoles in moderate yields. The reaction mechanism included generation of azomethine ylides, β-C-H functionalization of pyrrolidine, and sequential [3 + 2] cycloaddition. The obtained spirooxindole derivatives were investigated by in vitro evaluation against mouse colon cancer cells CT26 and human liver cancer cells HepG2 by MTT assay.

中文翻译：

通过[3 + 2]环加成反应和β-CH官能化吡咯烷合成7'-Arylidenespiro [吲哚啉-3,1'-吡咯嗪]和7'-Arylidenespiro [indene-2,1'-吡咯嗪]。

乙酸在回流的甲苯中催化吡咯烷，芳族醛和3-芳基氧杂吲哚-2-酮的三组分反应，可提供高收率和高非对映选择性的功能化7'-芳基螺[吲哚啉-3,1'-吡咯烷酮]。与2-亚芳基-1，3-茚满二酮的相似的三组分反应也以良好的产率得到了7'-亚芳基螺[茚-2,1'-吡咯烷酮]。然而，与3-苯乙叉基亚吲哚的反应以中等收率产生了螺[吲哚啉-3,1'-吡咯嗪]和7'-亚芳基取代的螺氧并吲哚的混合物。反应机理包括偶氮甲亚胺的生成，吡咯烷的β-CH官能化以及连续的[3 + 2]环加成反应。

更新日期：2019-09-19

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