Synthesis of an amino phosphinodiselenoic acid ester and β-amino diselenides employing P2Se5

被引:2
作者
Kumar, L. Roopesh [1 ]
Sagar, N. R. [1 ]
Divya, K. [1 ]
Madhu, C. [1 ]
Sureshbabu, Vommina V. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560056, Karnataka, India
关键词
ONE-POT; ENANTIOSELECTIVE ADDITION; UNSYMMETRICAL SELENOUREAS; CONVENIENT SYNTHESIS; PRIMARY SELENOAMIDES; EFFICIENT SYNTHESIS; SELENATING REAGENT; DERIVATIVES; SELENOCARBOXAMIDES; CONVERSION;
D O I
10.1039/d0nj00012d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of a new class of amino phosphinodiselenoic acid ester and beta-amino diselenides is conducted by employing a reaction between N-beta-protected aminoalkyl iodide and phosphorus pentaselenide (P2Se5) has been described. In the presence of protic solvents, amino phosphinodiselenoic acid esters were found to be the major products, whereas beta-amino diselenides were formed exclusively when the reaction was carried out in polar aprotic solvents.
引用
收藏
页码:7261 / 7264
页数:4
相关论文
共 46 条
[1]   Synthesis of α,α-disubstituted unnatural amino acid derivatives using the aza-[2,3]-Wittig sigmatropic rearrangement [J].
Anderson, JC ;
Skerratt, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2871-2879
[2]   Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy [J].
Baig, Nasir Rashid Baig ;
Chandrakala, R. N. ;
Sudhir, V. Sai ;
Chandrasekaran, Srinivasan .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2910-2921
[3]   An ebselen like catalyst with enhanced GPx activity via a selenol intermediate [J].
Balkrishna, Shah Jaimin ;
Kumar, Shailesh ;
Azad, Gajendra Kumar ;
Bhakuni, Bhagat Singh ;
Panini, Piyush ;
Ahalawat, Navjeet ;
Tomar, Raghuvir Singh ;
Detty, Michael R. ;
Kumar, Sangit .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (08) :1215-1219
[4]   Unusual Amino Acids in Medicinal Chemistry [J].
Blaskovich, Mark A. T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (24) :10807-10836
[5]   SELENOCYSTEINE - THE 21ST AMINO-ACID [J].
BOCK, A ;
FORCHHAMMER, K ;
HEIDER, J ;
LEINFELDER, W ;
SAWERS, G ;
VEPREK, B ;
ZINONI, F .
MOLECULAR MICROBIOLOGY, 1991, 5 (03) :515-520
[6]   Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].
Braga, AL ;
Paixao, MW ;
LUdtke, DS ;
Silveira, CC ;
Rodrigues, OED .
ORGANIC LETTERS, 2003, 5 (15) :2635-2638
[7]   Chiral diselenide ligands for the asymmetric copper-catalyzed conjugate addition of Grignard reagents to enones [J].
Braga, AL ;
Silva, SJN ;
Lüdtke, DS ;
Drekener, RL ;
Silveira, CC ;
Rocha, JBT ;
Wessjohann, LA .
TETRAHEDRON LETTERS, 2002, 43 (41) :7329-7331
[8]   Synthesis and application of chiral β-amino disulfides as ligands for the enantioselective addition of diethylzinc to aldehydes [J].
Braga, Antonio L. ;
Galetto, Fabio Z. ;
Rodrigues, Oscar E. D. ;
Silveira, Claudio C. ;
Paixao, Marcio W. .
CHIRALITY, 2008, 20 (07) :839-845
[9]   Unusual amino acids: Synthesis and introduction into naturally occurring peptides and biologically active analogues [J].
Cardillo, G ;
Gentilucci, L ;
Tolomelli, A .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2006, 6 (03) :293-304
[10]   Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics [J].
Chennakrishnareddy, Gundala ;
Nagendra, Govindappa ;
Hemantha, Hosahalli P. ;
Das, Ushati ;
Row, Tayur N. Guru ;
Sureshbabu, Vommina V. .
TETRAHEDRON, 2010, 66 (34) :6718-6724