New Synthesis of 2,4,6,8-Tetramethyl-2,4,6,8-tetra-azabicyclo[3.3.0]octane-3,7-dione Using Etidronic Acid as a "Green" Catalyst

被引：7
作者：
Panshina, S. Yu. [1 ,2 ]
Ponomarenko, O. V. [3 ]
Bakibaev, A. A. [1 ]
Malkov, V. S. [1 ]
机构：
[1] Natl Res Tomsk State Univ, Tomsk 634050, Russia
[2] Natl Res Tomsk Polytech Univ, Tomsk 634050, Russia
[3] Gumilyov Eurasian Natl Univ, Nur Sultan 010008, Kazakhstan
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 12期
关键词：
2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione; 1-hydroxyethane-1,1-diylbis(phosphonic acid); NMR; catalyst; hydantoin; glyoxal; N; '-dimethylurea; 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one; green chemistry;
D O I：
10.1134/S1070428020120039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method has been developed for the synthesis of 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione in 62% yield using etidronic acid [1-hydroxyethane-1,1-diylbis(phosphonic acid), HEDP] as a "green" catalyst. A plausible stepwise mechanism of the reaction has been proposed and partially confirmed by NMR data and studying model processes. The effects of the reaction medium and HEDP on particular species involved in the reaction, namely N,N'-dimethylurea, 4,5-dihydroxy-1,3-dimethylimidazolidin2-one, and 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione, have been studied by H-1 and C-13 NMR spectroscopy in D2O, neutral and acidified solutions (acetic acid-d(4)), and solutions containing 1 equiv of HEDP.
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页码：2067 / 2073
页数：7
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