Domino β‐C−H Functionalization and [3+2] Cycloaddition for Efficient Synthesis of Diverse Spiro and Polycyclic Compounds,ChemistrySelect

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Domino β‐C−H Functionalization and [3+2] Cycloaddition for Efficient Synthesis of Diverse Spiro and Polycyclic Compounds
ChemistrySelect ( IF 1.9 ) Pub Date : 2020-11-27 , DOI: 10.1002/slct.202003342
Hui‐Lin Fang ₁ , Ying Han ₁ , Jing Sun ₁ , Chao‐Guo Yan ₁

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The acetic acid catalyzed three‐component reaction of pyrrolidine, aromatic aldehydes and 4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐one in refluxing toluene gave functionalized 7′‐(E)‐benzylidenespiro[pyrazole‐4,1′‐pyrrolizines] in good yields and with high diastereoselectivity. The similar reaction with 2‐arylidene‐N,N’‐dimethylbarbiturates resulted in mixture of Z/E‐isomers of 7′‐ arylidenespiro[pyrimidine‐5,1′‐pyrrolizines] in good yields. However, the three‐component with N‐phenylmaleimides and sequential oxidation with DDQ reaction gave 8‐(E)‐arylidenedihydropyrrolo[3,4‐a]pyrrolizines in satisfactory yields. The reaction mechanism included sequential β‐C−H functionalization of pyrrolidine, generation of conjugated azomethine ylides, and sequential [3+2] cycloaddition with active alkenes.

中文翻译：

Dominoβ-CH功能化和[3 + 2]环加成反应可高效合成各种螺和多环化合物

乙酸在回流的甲苯中催化吡咯烷，芳族醛和4-亚芳基-5-甲基-2-苯基吡唑-3-酮的三组分反应，得到官能化的7'-（E）-苄叉基螺[吡唑-4,1'-吡咯嗪[]的收率高，非对映选择性高。与2-亚芳基-N，N'-二甲基巴比妥酸酯的类似反应导致7'-亚芳基螺[嘧啶-5,1'-吡咯烷酮]的Z / E异构体混合，收率很高。但是，三组分与N-苯基马来酰亚胺和DDQ反应的顺序氧化得到8-（E）-芳基二氢吡咯烷[3,4- a]吡咯烷酮，收率令人满意。该反应机理包括吡咯烷的顺序β-C-H官能化，共轭偶氮甲亚胺的生成以及与活性烯烃的顺序[3 + 2]环加成。

更新日期：2020-11-27

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