微波辅助新型含1,2,3-三唑基的α-氨基膦酸酯类化合物的合成及其晶体结构（英文）
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摘要
在微波辐射、无溶剂、无催化条件下,合成了两个新型含1,2,3-三唑基的α-氨基膦酸酯类化合物,结构经IR、NMR、X-射线晶体衍射进行了确证。O,O'-二异丙基-α-苯氨基-α-(2-苯基-1,2,3-三唑-4-基)-甲基膦酸酯(4a)晶体属三斜系,P-1空间群,晶胞参数为a=0. 94630(5) nm,b=1. 16572(6) nm,c=1. 17733(8) nm,α=109. 902(5)°,β=105. 410(5)°,γ=96. 748(5)°,V=1. 14586(12) nm~3,Z=2,C_(21)H_(27)N_4O_3P,Mr=414. 43,Dc=1. 201g·cm~3,F(000)=440,μ(Cu Kα)=1. 54184 mm~(-1)。O,O'-二异丙基-α-(4-氯苯基)氨基-α-(2-苯基-1,2,3-三唑-4-基)-甲基膦酸酯(4b)晶体属单斜系,P21/n空间群,晶胞参数为a=1. 11854(17) nm,b=2. 22135(3)nm,c=1. 90049(3) nm,β=91. 7350(15)°,V=4. 71995(12) nm~3,Z=8,C_(21)H_(26)ClN_4O_3P,Mr=448. 88,Dc=1. 263g·cm~3,F(000)=1888. 0,μ(Cu Kα)=1. 54184 mm~(-1)。
Two new α-aminophosphonates containing 1,2,3-triazole moietiey( 4 a,4 b) were designed and synthesized under microwave irradiation without solvents and catalysts.Their structures were verified by IR,NMR and single crystal X-ray diffraction.O,O'-Diisopropyl-α-phenylamino-α-( 2-phenyl-1,2,3-triazol-4-yl) methylphosphonate( 4 a) belongs to triclinic,space group P-1 with a =0. 94630( 5) nm,b = 1. 16572( 6) nm,c = 1. 17733( 8) nm,α = 109. 902( 5) °,β = 105. 410( 5) °,γ = 96. 748( 5) °,V = 1. 14586( 12)nm~3,Z= 2,C_(21)H_(27)N_4O_3 P,Mr = 414. 43,Dc = 1. 201 g·cm~3,F( 000) = 440 and μ( Cu Kα) = 1. 54184 mm~(-1). The crystal of O,O'-Diisopropyl-α-( 4-chloro-phenyl) amino-α-( 2-phenyl-1,2,3-triazol-4-yl) methyl phosphonate( 4 b) is of monoclinic,space group P21/n with a = 1. 11854( 17) nm,b = 2. 22135( 3) nm,c = 1. 90049( 3) nm,β = 91. 7350( 15) °,V = 4. 71995( 12) nm~3,Z = 8,C_(21)H_(26)ClN_4O_3 P,Mr= 448. 88,Dc= 1. 263 g·cm~3,F( 000) = 1888. 0 and μ( Cu Kα) = 1. 54184 mm~(-1).
Two new α-aminophosphonates containing 1,2,3-triazole moietiey( 4 a,4 b) were designed and synthesized under microwave irradiation without solvents and catalysts.Their structures were verified by IR,NMR and single crystal X-ray diffraction.O,O'-Diisopropyl-α-phenylamino-α-( 2-phenyl-1,2,3-triazol-4-yl) methylphosphonate( 4 a) belongs to triclinic,space group P-1 with a =0. 94630( 5) nm,b = 1. 16572( 6) nm,c = 1. 17733( 8) nm,α = 109. 902( 5) °,β = 105. 410( 5) °,γ = 96. 748( 5) °,V = 1. 14586( 12)nm~3,Z= 2,C_(21)H_(27)N_4O_3 P,Mr = 414. 43,Dc = 1. 201 g·cm~3,F( 000) = 440 and μ( Cu Kα) = 1. 54184 mm~(-1). The crystal of O,O'-Diisopropyl-α-( 4-chloro-phenyl) amino-α-( 2-phenyl-1,2,3-triazol-4-yl) methyl phosphonate( 4 b) is of monoclinic,space group P21/n with a = 1. 11854( 17) nm,b = 2. 22135( 3) nm,c = 1. 90049( 3) nm,β = 91. 7350( 15) °,V = 4. 71995( 12) nm~3,Z = 8,C_(21)H_(26)ClN_4O_3 P,Mr= 448. 88,Dc= 1. 263 g·cm~3,F( 000) = 1888. 0 and μ( Cu Kα) = 1. 54184 mm~(-1).
引文
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[4]Guo Y C,Li J,Ma J L,et al.Synthesis and antitumor activity of a-aminophosphonate derivatives Containing thieno[2,3-d]pyrimidines[J]. Chin Chem Lett,2015,26(3):755-758.
[5]Reddy K M K,Sadik S M,Saichaithanya N,et al.One-pot green synthesis and cytotoxicity of newα-aminophosphonates[J]. Res Chem Intermediate,2017,43(12):7087-7103.
[6]Wang Q M,Gao W,Song J L,et al.Synthesis,X-ray crystallographic analysis and BSA interaction of a newα-aminophosphonate[J].J Appl Spectrosc,2016,83(4):703-709.
[7]Subhashini N J P,Reddy Ch B,Kumar P A,et al.Synthesis and biological activity of new 2,6-diphenyl-4-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridines[J]. Rus J Gen Chem,2016,86(12):2845-2848.
[8]Xu Z,Lv Z S,Song X F,et al.Ciprofloxacin-isatin-1H-1,2,3-triazole hybrids:design,synthesis,and in vitro anti-tubercular activity against M. tuberculosis[J]. J Heterocycl Chem,2018,55(1):97-102.
[9]Mohammed I,Kummetha I R,Singh G,et al.1,2,3-triazoles as amide bioisosteres:discovery of a new class of potent HIV-1 Vif antagonists[J]. J Med Chem,2016,59(16):7677-7682.
[10]Kaushik C P,Pahwa A.Convenient synthesis,antimalarial and antimicrobial potential of thioethereal 1,4-disubstituted 1,2,3-triazoles with ester functionality[J]. Med Chem Res,2018,27(2):458-469.
[11]Sun Y,Jin Q H,Han Y,et al.Design,synthesis and antidepressant and anticonvulsant effect of 1-alkoxy-1H-benzo[d]-1,2,3-triazole derivatives[J].Lett Drug Des Discov,2017,14(3):314-322.
[12]Naveen P,Nikhila G,Udayakumar D,et al,Synthesis of novel 5-[(1,2,3-triazol-4-yl)methyl]-1-methyl-3H-pyridazino[4,5-b]indol-4-one derivatives by click reaction and exploration of their anticancer activity[J]. Med Chem Res,2016,25(1):135-148.
[13]Li Q H,Ding Y,Huang N W,Synthesis and biological activities of dithiocarbamates containing 1,2,3-triazoles group[J]. Chin Chem Lett,2014,25(11):1469-1472.
[14]El-Sayed W A,Khalaf H S,Mohamed S F,et al.Synthesis and antiviral activity of 1,2,3-triazole glycosides based substituted pyridine via click cycloaddition[J]. Rus J Gen Chem,2017,87(10):2444-2453.
[15]Dolomanov O V,Bourhis L J,Gildea R J,et al.Olex 2:a complete structure solution,refinement and analysis program[J]. J Appl Cryst,2009,42,339-341.
[16]Sheldrick G M.A short history of SHELX[J].Acta Cryst,2008,64(1):112-122.
[17]Sheldrick G M.Crystal structure refinement with SHELXL[J].Acta Cryst,2015,C71:3-8.
[18]Hong Y,Shangguan X C,Iqbai Z,et al.Synthesis,X-ray crystallographic analysis and bioactivities of-aminophosphonates featuring pyrazole and fluorine moieties[J].Chin J Struct Chem.2014,33(11):1673-1681.