Synthesis of novel α-aminophosphonates by methanesulfonic acid catalyzed Kabachnik-Fields reaction

被引：5

作者：

Ravi, Nuchu ^{[1
,2
]}

Venkatanarayana, Muvvala ^{[1
]}

Sharathbabu, Haridasyam ^{[1
]}

Babu, Kilaru Ravendra ^{[2
]}

机构：

[1] GITAM, GITAM Sch Sci, Dept Chem, Hyderabad, India

[2] Mylan Labs Ltd, ANRICH Ind Estate, CRD, Hyderabad, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2021年 / 196卷 / 11期

关键词：

Fluoro amines; alpha-aminophosphonate; CH3SO3H; catalysis; enantioselectivity; ONE-POT SYNTHESIS; 3-COMPONENT SYNTHESIS; AMINO PHOSPHONATES; ALDEHYDES; FLUORINE; DERIVATIVES; INHIBITORS; MECHANISM; ANALOGS;

D O I：

10.1080/10426507.2021.1960834

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of novel alpha-aminophosphonates of diethyl (2,4-difluorobenzylamino)methylphosphonate derivatives (4a-4g) have been synthesized by applying three-component Kabachnik-Fields reaction, using fluoro derivatives of aldehydes and substituted amines, diethyl phosphonate in the presence of a catalytic amount of methanesulfonic acid (MSA) in good yields with high enantioselectivities (up to 98% ee). The enantioselectivitiy of compounds (4a-4g) was confirmed by chiral HPLC. The direct Kabachnik-Fields reaction with high reactivity under mild reaction conditions and significantly used for synthesis of the alpha-aminophosphonate. The novel products were characterized by spectral and analytical data. [GRAPHICS] .

引用

页码：1018 / 1024

页数：7

共 50 条

[21] An ultra-sound assisted synthesis of α-aminophosphonates from benzyl halides via sequential Kornblum and Kabachnik-fields reaction
Amin, Rabia
Ara, Tabassum
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2023, 198 (05) : 417 - 423
[22] Tin(II) Compounds as Catalysts for the Kabachnik-Fields Reaction under Solvent-Free Conditions: Facile Synthesis of α-Aminophosphonates
Gallardo-Macias, Ricardo
Nakayama, Kensaku
SYNTHESIS-STUTTGART, 2010, (01): : 57 - 62
[23] Kinetics and the mechanism of Kabachnik-Fields reaction - V. Effect of the nature of hydrophosphoryl compound on the mechanism of Kabachnik-Fields reaction
Galkina, IV
Galkin, VI
Cherkasov, RA
ZHURNAL OBSHCHEI KHIMII, 1998, 68 (09): : 1469 - 1475
[24] Phosphomolybdic acid promoted Kabachnik-Fields reaction: an efficient one-pot synthesis of α-aminophosphonates from 2-cyclopropylpyrimidine-4-carbaldehyde
Reddy, Pogula Sreekanth
Reddy, Peddiahgari Vasu Govardhana
Reddy, Sura Mallikarjun
TETRAHEDRON LETTERS, 2014, 55 (22) : 3336 - 3339
[25] Alkyl alkynylphosphonites in the Kabachnik-Fields reaction
Trishin, YG
Maslov, VI
RUSSIAN CHEMICAL BULLETIN, 1998, 47 (10) : 2047 - 2048
[26] The Kabachnik-Fields Reaction: Mechanism and Synthetic Use
Keglevich, Gyoergy
Balint, Erika
MOLECULES, 2012, 17 (11) : 12821 - 12835
[27] Kinetics and the mechanism of Kabachnik-Fields reaction - II. Kabachnik-Fields reaction in the dialkylphosphite-benzaldehyde-cyclohexylamine system
Galkina, IV
Zvereva, ER
Galkin, VI
Sobanov, AA
Cherkasov, RA
ZHURNAL OBSHCHEI KHIMII, 1998, 68 (09): : 1453 - 1456
[28] Synthesis of hydrophospohoryl derivatives of the antifungal antibiotic pimaricin by the Kabachnik-Fields reaction
Belakhov, V. V.
Shenin, Yu. D.
Ionin, B. I.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (02) : 305 - 312
[29] On the reversibility of hydroxyphosphonate formation in the Kabachnik-Fields reaction
Gancarz, R
Gancarz, I
Walkowiak, U
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 104 (1-4): : 45 - 52
[30] TBAPMNP as an Effective and Recyclable Heterogeneous Catalyst for Single-Pot Three Component Synthesis of α-Aminophosphonates through Kabachnik-Fields Reaction
Agrwal, A.
Chadha, N.
Sahu, A.
Kumar, V.
Kasana, V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2023, 93 (11) : 2859 - 2865

← 1 2 3 4 5 →