The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

被引：47

作者：

Balint, Erika ^{[1
]}

Tajti, Adam ^{[2
]}

Adam, Anna ^{[2
]}

Csontos, Istvan ^{[2
]}

Karaghiosoff, Konstantin ^{[3
]}

Czugler, Matyas ^{[2
]}

Abranyi-Balogh, Peter ^{[4
]}

Keglevich, Gyorgy ^{[2
]}

机构：

[1] MTA BME Res Grp Organ Chem Technol, H-1521 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary

[3] Ludwig Maximilians Univ Munchen, Dept Chem, D-81377 Munich, Germany

[4] Hungarian Acad Sci, Inst Organ Chem, Res Ctr Nat Sci, H-1519 Budapest, Hungary

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

基金：

匈牙利科学研究基金会;

关键词：

alpha-aryl-alpha-aminophosphine oxides; alpha-aryl-alpha-aminophosphonates; microwave; Pudovik reaction; CATALYZED ENANTIOSELECTIVE HYDROPHOSPHONYLATION; KABACHNIK-FIELDS REACTION; SCHIFF-BASES; IMINES; MECHANISM; ACCESS; DERIVATIVES; PHOSPHITES; INHIBITORS; BEARING;

D O I：

10.3762/bjoc.13.10

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A family of alpha-aryl-alpha-aminophosphonates and alpha-aryl-alpha-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two alpha-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H center dot center dot center dot O=P intermolecular hydrogen bridges pair.

引用

页码：76 / 86

页数：11

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