CeCl3•7H2O CATALYZED, MICROWAVE-ASSISTED HIGH-YIELD SYNTHESIS OF α-AMINOPHOSPHONATES AND THEIR BIOLOGICAL STUDIES

被引：12

作者：

Varalakshmi, M. ^{[1
]}

Srinivasulu, D. ^{[1
]}

Rajasekhar, D. ^{[1
]}

Raju, C. Naga ^{[1
]}

Sreevani, S. ^{[2
]}

机构：

[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India

[2] Sri Venkateswara Univ, Dept Microbiol, Tirupati 517502, Andhra Pradesh, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2014年 / 189卷 / 01期

关键词：

-Aminophosphonates; Lewis acid catalyst (CeCl3 center dot 7H(2)O); microwave irradiation; antimicrobial and antioxidant activities; SCAVENGING PROPERTIES; AMINO PHOSPHONATES; CHLORIDE; BROMOPHENOLS; SYSTEM; ACID;

D O I：

10.1080/10426507.2013.798785

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new class of diethyl(3,5-dibromo-4-hydroxyphenylamino) (substituted phenyl/heterocyclic) methylphosphonates 4(a-j) has been synthesized by one-pot three component simultaneous reaction (Kabachnik-Fields) of 4-amino-2,6-dibromophenol 1, substituted heterocyclic/phenyl aldehydes 2(a-j), and diethylphosphite 3 using a Lewis acid catalyst, CeCl(3)7H(2)O (5mol%) under microwave irradiation as well as conventional conditions. It was observed that microwave irradiation method is more facile, efficient, and advantageous with respect to reaction time and yields. The structures of all the synthesized compounds were supported by analyzing IR, H-1/C-13/P-31 NMR, and mass spectral data. The synthesized compounds were screened for their in vitro antimicrobial and antioxidant activities.

引用

页码：106 / 112

页数：7

共 39 条

[1] Abbas A.J., 2010, HETEROATOM CHEM, V21, P397, DOI [10.1002/hc.20635, DOI 10.1002/HC.20635]
[2] One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina
Ambica
Kumar, Satish
Taneja, Subhash C.
Hundal, Maninder S.
Kapoor, Kamal K.
[J]. TETRAHEDRON LETTERS, 2008, 49 (14) : 2208 - 2212
[3] [Anonymous], CHEM ORGANOPHOSPHORU
[4] [Anonymous], 2000, Approved Standard M7-A5
[5] [Anonymous], 2009, Bioorg. Med. Chem. Lett., DOI DOI 10.1016/J.BMCL
[6] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID
ATHERTON, FR
HASSALL, CH
LAMBERT, RW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) : 29 - 40
[7] Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions
Bartoli, G
Bartolacci, M
Giuliani, A
Marcantoni, E
Massaccesi, M
Torregiani, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) : 169 - 174
[8] The CeCl3•nH2O/NaI system in organic synthesis:: An efficient water tolerant Lewis acid promoter
Bartoli, G
Marcantoni, E
Sambri, L
[J]. SYNLETT, 2003, (14) : 2101 - 2116
[9] BAUER AW, 1966, AM J CLIN PATHOL, V45, P493
[10] Bloemink MJ, 1999, EUR J INORG CHEM, P1655

← 1 2 3 4 →