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高效构建多样的螺[吲哚啉-3,4'-吡咯并[3,4-]吡啶][3 + 3]环加成物:色胺 MBH 碳酸酯与β-烯胺马来酰亚胺的反应。

Efficient construction of diverse spiro[indoline-3,4'-pyrrolo[3,4-]pyridines] [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides.

机构信息

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.

出版信息

Org Biomol Chem. 2022 Sep 14;20(35):7099-7104. doi: 10.1039/d2ob01257j.

DOI:10.1039/d2ob01257j
PMID:36040323
Abstract

An efficient method to construct unique spiro[indoline-3,4'-pyrrolo[3,4-]pyridines] was successfully developed a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates of isatins with β-enamino maleimides in acetonitrile at room temperature. This reaction afforded multifunctionalized spiro[indoline-3,4'-pyrrolo[3,4-]pyridines] and spiro[dipyrrolo[3,4-:3',4'-]pyridine-8,3'-indolines] in good yields and with lower diastereoselectivity. The relative configuration of the two diasteromers of the spiro compounds was clearly elucidated by the determination of eight single crystal structures.

摘要

一种高效的方法成功地构建了独特的螺[吲哚啉-3,4'-吡咯并[3,4-]吡啶],该方法是通过 DABCO 促进的色酮与β-烯胺马来酰亚胺的[3 + 3]环加成反应在室温下在乙腈中实现的。该反应以良好的收率和较低的非对映选择性得到了多官能化的螺[吲哚啉-3,4'-吡咯并[3,4-]吡啶]和螺[二吡咯并[3,4-:3',4'-]吡啶-8,3'-吲哚啉]。通过确定八个单晶结构,清楚地阐明了螺化合物的两个非对映异构体的相对构型。

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