Tandem nucleophilic addition/oxa-Michael reaction of ortho-formyl chalcones with dimethyl (diazomethyl)phosphonate for the synthesis of phosphine-containing 1,3-disubstituted phthalans

被引：5

作者：

Wei, Ximeng ^{[1
]}

Chen, Guihua ^{[1
]}

Peng, Yungui ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 33期

基金：

中国国家自然科学基金;

关键词：

Tandem reaction; Ortho-formyl chalcones; Dimethyl (diazomethyl)phosphonate; Phosphine-containing 1,3-disubstituted phthalans; SEROTONIN REUPTAKE INHIBITOR; ASYMMETRIC MANNICH REACTION; ONE-POT CONVERSION; ALPHA-DIAZOMETHYLPHOSPHONATES; PESTALOTIOPSIS-MICROSPORA; STEREOSELECTIVE-SYNTHESIS; ALKYNES; ROUTE; 1,3-DIHYDROISOBENZOFURANS; ANTIOXIDANT;

D O I：

10.1016/j.tetlet.2020.152174

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel base-promoted tandem reaction between ortho-formyl chalcones and dimethyl (diazomethyl) phosphonate has been discovered for the construction of a series of phosphine-containing 1,3-disubstituted phthalans with up to 99% yields. This reaction was amenable to scale up to 1 mmol with 90% yield. The alkyne, which was well-known as the product of Seyferth-Gilbert reagent with aldehyde, was not detected in this reaction. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：4

共 2 条

[1] Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans
Gharpure, Santosh J.
Prasad, J. V. K.
Bera, Kalisankar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3570 - 3574
[2] Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones Catalyzed by a Chiral Phosphoric Acid
Yang, Xing
Pang, Shuai
Cheng, Feng
Zhang, Yue
Lin, Ya-Wei
Yuan, Quan
Zhang, Fang-Lin
Huang, Yi-Yong
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10388 - 10397

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