Efficient Synthesis of Substituted Cyclic α-Aminophosphonates

被引：28

作者：

Odinets, Irina L. ^{[1
]}

Artyushin, Oleg I. ^{[1
]}

Shevchenko, Nikolay ^{[2
]}

Petrovskii, Pavel V. ^{[1
]}

Nenajdenko, Valentin G. ^{[2
]}

Roeschenthaler, Gerd-Volker ^{[3
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Moscow 119992, Russia

[3] Univ Bremen, Inst Inorgan & Phys Chem, D-28334 Bremen, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 04期

关键词：

diethyl phosphonate; cyclic imines; addition reactions; alpha-aminophosphonates; ASYMMETRIC-SYNTHESIS; AZIRIDINE; 2-PHOSPHONATES; ACIDS; ANALOGS; DERIVATIVES; INHIBITORS; CRYSTAL; IMINES; ESTERS; ROUTE;

D O I：

10.1055/s-0028-1083349

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of diethyl phosphite to cyclic imines bearing alkyl, aryl, or heteroaryl substituents at the alpha-position in diethyl ether at room temperature presents an efficient route to substituted cyclic alpha-aminophosphonates. The application of boron trifluoride diethyl ether complex as a catalyst significantly accelerates the reaction.

引用

页码：577 / 582

页数：6

共 50 条

[31] One Pot Green Synthesis of α-Aminophosphonates with D-Malic Acid as an Organocatalyst
Mudila, Harish
Kapoor, Himanshu
Prasher, Parteek
RECENT ADVANCES IN FUNDAMENTAL AND APPLIED SCIENCES (RAFAS 2016), 2017, 1860
[32] A NOVEL AND EFFICIENT SYNTHESIS OF α-AMINOPHOSPHONATES BY USE OF TRIPHENYL PHOSPHITE IN ACETIC ACID MEDIA
Rostamizadeh, Mohsen
Maghsoodlou, Malek Taher
Hazeri, Nourallah
Habibi-khorassani, Sayyed Mostafa
Keishams, Leila
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (02) : 334 - 337
[33] Synthesis of trifluoromethyl γ-aminophosphonates by nucleophilic aziridine ring opening
Cytlak, T.
Saweliew, M.
Kubicki, M.
Koroniak, H.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (39) : 10050 - 10059
[34] Design and one-pot synthesis of α-aminophosphonates and bis (α-aminophosphonates) by iron(III) chloride and cytotoxic activity
Rezaei, Zahra
Firouzabadi, Habib
Iranpoor, Nasser
Ghaderi, Abbas
Jafari, Mohammad Reza
Jafari, Abbas Ali
Zare, Hamid Reza
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) : 4266 - 4275
[35] Manganese-proline derived new catalyst system for the enantioselective synthesis of α-hydroxyphosphonates and α-aminophosphonates
Lim, Hyun
Datilus, Vicklyn
Teriak, Rania
Chohan, Prianka
Kaur, Parminder
TETRAHEDRON LETTERS, 2017, 58 (15) : 1480 - 1483
[36] Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates
Yao, Gui-yang
Ye, Man-yi
Huang, Ri-zhen
Li, Ya-jun
Pan, Ying-ming
Xu, Qing
Liao, Zhi-Xin
Wang, Heng-shan
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (02) : 501 - 507
[37] Synthesis of Cyclic α-Aminophosphonates through Copper-Catalyzed Enamine Activation
Han, Junbin
Paton, Robert S.
Xu, Bo
Hammond, Gerald B.
SYNTHESIS-STUTTGART, 2013, 45 (04): : 463 - 470
[38] Magnetic ZnO@CuO@Iron ore nanocomposites as a green and highly efficient heterogeneous nanocatalyst for solventless synthesis of α-aminophosphonates
Sajadi, S. Mohammad
JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (1-2) : 25 - 30
[39] HIGHLY EFFICIENT ONE-POT SYNTHESIS OF α-AMINOPHOSPHONATES CATALYZED BY YTTERBIUM TRIFLATE IN WATER
Shen, MingGui
Shang, ShiBin
Song, ZhanQian
Wang, Dan
Rao, XiaoPing
Gao, Hong
Wang, Juan
SYNTHETIC COMMUNICATIONS, 2014, 44 (03) : 361 - 367
[40] Phenylboronic Acid as Efficient and Eco-Friendly Catalyst for the One-Pot, Three-Component Synthesis of α-Aminophosphonates under Solvent-Free Conditions
Tibhe, Gaurao D.
Bedolla-Medrano, Mercedes
Cativiela, Carlos
Ordonez, Mario
SYNLETT, 2012, (13) : 1931 - 1936

← 1 2 3 4 5 →