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Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones
Synthesis ( IF 2.2 ) Pub Date : 2018-07-12 , DOI: 10.1055/s-0037-1610438
Ying Han , Chao-Guo Yan , Chang-Zhou Liu , Yuan-Yuan Zhang , Jing Sun

Abstract

The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.

The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.



中文翻译:

乙二酸二烷基酯与3-芳基氨基-1-甲基-1H-吡咯-2,5-二酮的亲核膦促进多米诺反应

摘要

三苯基膦的三组分反应,乙炔二和三芳基氨基-1-甲基- 1 H ^ -吡咯-2,5-二酮在CH 22在室温下导致官能3-(三苯基-λ 5 -phosphanylidene)琥珀酸酯的收率接近定量。然而,三(丁基)膦在CH 2 Cl 2中促进了乙炔二羧酸二烷基酯与3-芳基氨基-1-甲基-1 H-吡咯-2,5-二酮的反应,提供了官能化的吡咯并[3,4- b ]吡啶- 4-羧酸盐具有令人满意的产率。

三苯基膦的三组分反应,乙炔二和三芳基氨基-1-甲基- 1 H ^ -吡咯-2,5-二酮在CH 22在室温下导致官能3-(三苯基-λ 5 -phosphanylidene)琥珀酸酯的收率接近定量。然而,三(丁基)膦在CH 2 Cl 2中促进了乙炔二羧酸二烷基酯与3-芳基氨基-1-甲基-1 H-吡咯-2,5-二酮的反应,提供了官能化的吡咯并[3,4- b ]吡啶- 4-羧酸盐具有令人满意的产率。

更新日期:2018-07-12
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