One-Pot Synthesis of Pyrazolyl-Containing α-Aminophosphonates

Abstract A series of novel pyrazolyl-containing α-aminophosphonates were synthesized by one-pot reaction from 4-formylpyrazole, substituted aromatic amines, and dialkylphosphites. The synthesized compounds were characterized by elemental analysis, 1H NMR, and IR spectroscopy. Single-crystal X-ray diffraction data of compounds 4a and 5b were obtained, and some of these compounds showed inhibitory effect on eggplant-infecting Botrytis cinerea. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Tables S1-S4. Figures S1 and S2 .cif files. GRAPHICAL ABSTRACT

[1]  S. Al-Deyab,et al.  2-Aminopyrimidinium dihydrogen phosphate monohydrate , 2011, Acta crystallographica. Section E, Structure reports online.

[2]  O. García-Barradas,et al.  Uncatalyzed One-Pot Diastereoselective Synthesis of α-Amino Phosphonates Under Solvent-Free Conditions , 2010 .

[3]  L. Cao,et al.  Synthesis of Chromonyl-Containing α-Aminophosphonates , 2009 .

[4]  Scott Boyd,et al.  A one step synthesis of 1-alkylpyrazolo[5,4-d]pyrimidines , 2008 .

[5]  Jun-Ying Miao,et al.  Synthesis and preliminary biological evaluation of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as potential agents against A549 lung cancer cells. , 2008, Bioorganic & medicinal chemistry.

[6]  Cun‐Kui Li,et al.  Synthesis and Fluorescent Properties of 2-Arylamino-5-(3-Aryl-1-Phenyl-Pyrazol-4-Yl)-1,3,4-Thiadiazoles , 2008 .

[7]  Pinaki S. Bhadury,et al.  Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group. , 2008, Bioorganic & medicinal chemistry.

[8]  A. Bazgir,et al.  One-pot synthesis and antibacterial activities of pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine-dione derivatives. , 2008, Bioorganic & medicinal chemistry letters.

[9]  A. Bhattacharya,et al.  Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot , 2008 .

[10]  Zhiwei Miao,et al.  An improved route to the synthetic of diphenyl α-(diethoxythiophosphorylamino)methylphosphonates , 2006 .

[11]  Wei Zhang,et al.  Microwave-assisted solvent-free and catalyst-free Kabachnik–Fields reactions for α-amino phosphonates , 2006 .

[12]  S. Chandrasekhar,et al.  Solvent and catalyst free three-component coupling of carbonyl compounds, amines and triethylphosphite; A new synthesis of α-aminophosphonates , 2003 .

[13]  J. Katzenellenbogen,et al.  Diaryl-dialkyl-substituted pyrazoles: regioselective synthesis and binding affinity for the estrogen receptor. , 2002, Bioorganic & medicinal chemistry letters.

[14]  M. Horiguchi,et al.  Isolation of 2-Aminoethane Phosphonic Acid from Rumen Protozoa , 1959, Nature.

[15]  D. A. Shirley Preparation of organic intermediates , 1951 .