Synthesis of 5‐Organotellanyl‐1H‐1,2,3‐tri­azoles: Functionalization of the 5‐Position Scaffold by the Sonogashira Cross‐Coupling Reaction

作者: Hélio A. Stefani , Stanley N. S. Vasconcelos , Flávia Manarin , Daiana M. Leal , Frederico B. Souza

DOI: 10.1002/EJOC.201300009

关键词:

摘要: An efficient synthesis of 5-organotellanyl-1H-1,2,3-triazole compounds was accomplished through [3+2] cycloaddition reaction organic azides and (organotellanyl)alkynes. Additionally, 5-organotellanyl-1H-1,2,3-triazoles were readily functionalized at the 5-position by using a Sonogashira cross-coupling reaction, leading to highly functionalised triazoles. The regiochemistry products assessed two-dimensional NMR spectroscopic experiments X-ray crystallography.

参考文章(38)
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
Changwei Shao, Guolin Cheng, Deyong Su, Jimin Xu, Xinyan Wang, Yuefei Hu, Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper‐Catalyzed Azide‐Alkyne Cycloaddition Advanced Synthesis & Catalysis. ,vol. 352, pp. 1587- 1592 ,(2010) , 10.1002/ADSC.200900768
Rosa Alvarez, Sonsoles Velazquez, Ana San-Felix, Stefano Aquaro, Erik De Clercq, Carlo-Federico Perno, Anna Karlsson, Jan Balzarini, Maria Jose Camarasa, 1,2,3-Triazole-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D- ribofuranosyl]-3'-spiro-5"-(4"-amino-1",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity. Journal of Medicinal Chemistry. ,vol. 37, pp. 4185- 4194 ,(1994) , 10.1021/JM00050A015
Rajeev Kharb, Prabodh Chander Sharma, Mohammed Shahar Yar, Pharmacological significance of triazole scaffold. Journal of Enzyme Inhibition and Medicinal Chemistry. ,vol. 26, pp. 1- 21 ,(2011) , 10.3109/14756360903524304
Xu Zhao, Bo Wei Lu, Jun Rui Lu, Chun Wei Xin, Jian Fa Li, Ya Liu, Design, synthesis and antimicrobial activities of 1,2,3-triazole derivatives Chinese Chemical Letters. ,vol. 23, pp. 933- 935 ,(2012) , 10.1016/J.CCLET.2012.06.014
Jun Terao, Nobuaki Kambe, Noboru Sonoda, Tellurium-zinc exchange reaction. A new preparative method of alkenylzinc reagents Tetrahedron Letters. ,vol. 37, pp. 4741- 4744 ,(1996) , 10.1016/0040-4039(96)00955-0
Michael J. Genin, Debra A. Allwine, David J. Anderson, Michael R. Barbachyn, D. Edward Emmert, Stuart A. Garmon, David R. Graber, Kevin C. Grega, Jackson B. Hester, Douglas K. Hutchinson, Joel Morris, Robert J. Reischer, Charles W. Ford, Gary E. Zurenko, Judith C. Hamel, Ronda D. Schaadt, Douglas Stapert, Betty H. Yagi, Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. Journal of Medicinal Chemistry. ,vol. 43, pp. 953- 970 ,(2000) , 10.1021/JM990373E
Miguel J Dabdoub, Vânia B Dabdoub, Joseph P Marino, None, Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds Tetrahedron Letters. ,vol. 41, pp. 437- 440 ,(2000) , 10.1016/S0040-4039(99)02088-2
Fateh V. Singh, Mônica F.Z.J. Amaral, Hélio A. Stefani, Synthesis of symmetrical 1,3-diynes via homocoupling reaction of n-butyl alkynyltellurides Tetrahedron Letters. ,vol. 50, pp. 2636- 2639 ,(2009) , 10.1016/J.TETLET.2009.03.078
Marcio S. Silva, Renan S. Ferrarini, Bruno A. Sousa, Fabiano T. Toledo, João V. Comasseto, Rogério A. Gariani, Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system Tetrahedron Letters. ,vol. 53, pp. 3556- 3559 ,(2012) , 10.1016/J.TETLET.2012.04.134