Diastereoselective synthesis of dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidine] via [3 + 2]cycloaddition reaction of MBH maleimides of isatins and 1,3-dicarbonyl compounds,Organic Chemistry Frontiers

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Diastereoselective synthesis of dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidine] via [3 + 2]cycloaddition reaction of MBH maleimides of isatins and 1,3-dicarbonyl compounds
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-09-08 , DOI: 10.1039/d0qo00845a
Liu-Na Pan _{1,

2,

3,

4} , Jing Sun _{1,

2,

3,

4} , Rong-Guo Shi _{1,

2,

3,

4} , Chao-Guo Yan _{1,

2,

3,

4}

Affiliation

In the presence of mixed bases DABCO and K₂CO₃, the reaction of MBH maleimides of isatins with various cyclic 1,3-dicarbonyl compounds such as 1,3-cyclohexanedione, dimedone, 4-hydroxychromenone and benzoylacetonitrile afforded functionalized dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidines] in satisfactory yields and with high diastereoselectivity. This formal [3 + 2]cycloaddition proceeded with nucleophilic substitution of an allylammonium ylide and oxa-Michael addition of an enolate. However, a similar reaction of MBH adducts of isatins derived from acrylonitrile and methyl acrylate resulted in functionalized spiro[indoline-3,4′-pyranes] in good yields through formal [3 + 3]cycloaddition reaction.

中文翻译：

通过靛红与1,3-二羰基化合物的MBH马来酰亚胺的[3 + 2]环加成反应，非对映选择性合成二螺[吲哚啉-3,3'-呋喃-2'，3''-吡咯烷]

在混合碱DABCO和K ₂ CO ₃的存在下，靛红的MBH马来酰亚胺与各种环状1,3-二羰基化合物（例如1,3-环己二酮，二甲酮，4-羟基色酮和苯甲酰基乙腈）的反应提供了功能化的双螺[吲哚3，3′-呋喃-2′，3′′-吡咯烷]以令人满意的产率和高非对映选择性。正式的[3 + 2]环加成反应是对烯丙基乙胺盐进行亲核取代，对烯醇盐进行oxa-Michael加成。然而，通过正式的[3 + 3]环加成反应，衍生自丙烯腈和丙烯酸甲酯的isatins的MBH加合物的类似反应导致官能化的螺[吲哚啉-3,4'-吡喃]收率很高。

更新日期：2020-10-13

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