In situ generation of trityl carbocation (Ph3C+) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s

doi:10.1016/S1872-2067(12)60728-1

催化学报 ›› 2014, Vol. 35 ›› Issue (1): 85-89.DOI: 10.1016/S1872-2067(12)60728-1

In situ generation of trityl carbocation (Ph₃C⁺) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s

Abdolkarim Zare^a, Maria Merajoddin^a, Ahmad Reza Moosavi-Zare^b, Mahmoud Zarei^c

a Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran;
b Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran;
c Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran

收稿日期:2013-08-11 修回日期:2013-09-11 出版日期:2013-12-23 发布日期:2014-01-17
通讯作者: Abdolkarim Zare

In situ generation of trityl carbocation (Ph₃C⁺) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s

Abdolkarim Zare^a, Maria Merajoddin^a, Ahmad Reza Moosavi-Zare^b, Mahmoud Zarei^c

a Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran;
b Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran;
c Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran

Received:2013-08-11 Revised:2013-09-11 Online:2013-12-23 Published:2014-01-17
Contact: Abdolkarim Zare

摘要/Abstract

摘要：

Trityl chloride (Ph₃CCl) efficiently catalyzes the condensation of 3-methyl-1-phenyl-1H-pyrazol- 5(4H)-one and aromatic aldehydes under mild and solvent-free conditions, affording 4,4'- (arylmethylene)-bis(3-methyl-1-phenyl-1H- pyrazol-5-ol)s in high to excellent yields and in short reaction time. The presence of the requisite organocatalytic trityl carbocation (Ph₃C⁺) species was confirmed by analysis of infrared, ¹H NMR, and ultra violet spectral data. A plausible mechanism was proposed for the reaction based on the observations and literature precedent.

关键词: Trityl chloride (Ph₃CCl), Trityl carbocation (Ph₃C⁺), 4,4'-(Arylmethylene)-bis(3- methyl-1-phenyl-1H-pyrazol-5-ol), 3-Methyl-1-phenyl-1H-pyrazol-5(4H)-one, Solvent-free synthesis

Abstract:

Key words: Trityl chloride (Ph₃CCl), Trityl carbocation (Ph₃C⁺), 4,4'-(Arylmethylene)-bis(3- methyl-1-phenyl-1H-pyrazol-5-ol), 3-Methyl-1-phenyl-1H-pyrazol-5(4H)-one, Solvent-free synthesis

Abdolkarim Zare, Maria Merajoddin, Ahmad Reza Moosavi-Zare, Mahmoud Zarei. In situ generation of trityl carbocation (Ph₃C⁺) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s[J]. 催化学报, 2014, 35(1): 85-89.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(12)60728-1

https://www.cjcatal.com/CN/Y2014/V35/I1/85

参考文献

[1] Jacobsen E N, MacMillan D W C. Proc Natl Acad Sci USA, 2010, 107: 20618
[2] Kargar M, Hekmatshoar R, Mostashari A, Hashemi Z. Catal Commun, 2011, 15: 123
[3] Singh K N, Singh P, Singh P, Lal N, Sharma S K. Bioorg Med Chem Lett, 2012, 22: 4225
[4] Sohtome Y, Tanatani A, Hashimoto Y, Nagasawa K. Tetrahedron Lett, 2004, 45: 5589
[5] Huang Y B, Yi W B, Cai C. J Fluorine Chem, 2010, 131: 879
[6] Miura T, Nishida S, Masuda A, Tada N, Itoh A. Tetrahedron Lett, 2011, 52: 4158
[7] Thorat P B, Goswami S V, Khade B C, Bhusare S R. Tetrahedron Lett, 2012, 53: 6083
[8] Verma S, Jain S L, Sain B. Tetrahedron Lett, 2010, 51: 6897
[9] Khalafi-Nezhad A, Parhami A, Zare A, Moosavi Zare A R, Hasaninejad A, Panahi F. Synthesis, 2008: 617
[10] Khalafi-Nezhad A, Parhami A, Zare A, Nasrollahi Shirazi A, Moosavi Zare A R, Hasaninejad A. Can J Chem, 2008, 86: 456
[11] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Parhami A, Khalafi-Nezhad A. Appl Catal A, 2010, 386: 179
[12] Zare A, Merajoddin M, Abi F, Moosavi-Zare A R, Mokhlesi M, Zolfigol M A, Asgari Z, Khakyzadeh V, Hasaninejad A, Khalafi-Nezhad A, Parhami A. J Chin Chem Soc, 2012, 59: 860
[13] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Khojasteh M, Asgari Z, Khakyzadeh V, Khalafi-Nezhad A. Catal Commun, 2012, 20: 54
[14] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Abi F, Zare A, Kaveh H, Khakyzadeh V, Kazem-Rostami M, Parhami A, Torabi-Monfared H. Tetrahedron, 2013, 69: 212
[15] Zare A, Merajoddin M, Hasaninejad A, Moosavi-Zare A R, Khakyzadeh V. C R Chim, 2013, 16: 380
[16] Park H J, Lee K, Park S J, Ahn B, Lee J C, Cho H Y, Lee K I. Bioorg Med Chem Lett, 2005, 15: 3307
[17] Chauhan P M S, Singh S, Chatterjee R K. Ind J Chem, Sect B, 1993, 32: 858
[18] Mahajan R N, Havaldar F H, Fernandes P S. J Ind Chem Soc, 1991, 68: 245
[19] Bailey D M, Hansen P E, Hlavac A G, Baizman E R, Pearl J, DeFelice A F, Feigenson M E. J Med Chem, 1985, 28: 256
[20] Cho I H, Noh J Y, Park S W, Ryu H C, Lim J W, Kim J H, Chae M Y, Kim D H, Jung S H, Park H J, Kim Y H, Min I K. US Patent 2 004 002 532. 2004
[21] Clark M P, Laughlin S K, Golebiowski A, Brugel T A, Sabat M. WO Patent 2 005 047 287. 2005
[22] Rosiere C E, Grossman M I. Science, 1951, 113: 651
[23] Uzoukwu A B, Al-Juaid S S, Hitchcock P B, Smith J D. Polyhedron, 1993, 12: 2719
[24] Singh D, Singh D. J Ind Chem Soc, 1991, 68: 165
[25] Londershausen M. Pestic Sci, 1996, 48: 269
[26] Sujatha K, Shanthi G, Selvam N P, Manoharan S, Perumal P T, Rajendran M. Bioorg Med Chem Lett, 2009, 19: 4501
[27] Sobhani S, Safaei E, Hasaninejad A R, Rezazadeh S. J Organomet Chem, 2009, 694: 3027
[28] Sobhani S, Hasaninejad A R, Maleki M F, Parizi Z P. Synth Commun, 2012, 42: 2245
[29] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Asgari Z, Shekouhy M, Zare A, Hasaninejad A. RSC Adv, 2012, 2: 8010
[30] Karimi-Jaberi Z, Pooladian B, Moradi M, Ghasemi E. Chin J Catal (催化学报), 2012, 33: 1945
[31] Niknam K, Saberi D, Sadegheyan M, Deris A. Tetrahedron Lett, 2010, 51: 692
[32] Hasaninejad A, Shekouhy M, Zare A, Hoseini Ghattali S M S, Golzar N. J Iran Chem Soc, 2011, 8: 411
[33] Kuarm B S, Rajitha B. Synth Commun, 2012, 42: 2382
[34] Tayebi S, Baghernejad M, Saberi D, Niknam K. Chin J Catal (催化学报), 2011, 32: 1477
[35] Hasaninejad A, Zare A, Shekouhy M, Golzar N. Org Prep Proced Int, 2011, 43: 131
[36] Oikawa M, Yoshizaki H, Kusumoto S. Synlett, 1998: 757
[37] Hasaninejad A, Rasekhi Kazerooni M, Zare A. ACS Sustainable Chem Eng, 2013, 1: 679

In situ generation of trityl carbocation (Ph₃C⁺) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s

In situ generation of trityl carbocation (Ph₃C⁺) as a homogeneous organocatalyst for the efficient synthesis of 4, 4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 2

编辑推荐

Metrics

[1]	Hamid Reza Shaterian, Morteza Aghakhanizadeh. Ionic-liquid-catalyzed green synthesis of coumarin derivatives under solvent-free conditions[J]. 催化学报, 2013, 34(9): 1690-1696.
[2]	Ardeshir Khazaei, Mohammad Ali Zolfigol, Ahmad Reza Moosavi-Zare, Javad Afsar, Abdolkarim Zare, Vahid Khakyzadeh, Mohammad Hassan Beyzavi. Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst[J]. 催化学报, 2013, 34(10): 1936-1944.