One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br3 under solvent-free conditions

doi:10.1016/S1872-2067(14)60029-2

催化学报 ›› 2014, Vol. 35 ›› Issue (7): 1024-1029.DOI: 10.1016/S1872-2067(14)60029-2

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions

Arash Ghorbani-Choghamarani, Shima Rashidimoghadam

Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran

收稿日期:2013-12-17 修回日期:2014-01-09 出版日期:2014-06-28 发布日期:2014-06-28
通讯作者: Arash Ghorbani-Choghamarani
基金资助:
This work was supported by Research Facilities of Ilam University, Ilam, Iran.

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions

Arash Ghorbani-Choghamarani, Shima Rashidimoghadam

Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran

Received:2013-12-17 Revised:2014-01-09 Online:2014-06-28 Published:2014-06-28
Supported by:
This work was supported by Research Facilities of Ilam University, Ilam, Iran.

摘要/Abstract

摘要：

A facile and efficient method has been developed for the synthesis of 1-amidoalkyl-2-naphthols via the one-pot multi-component condensation of 2-naphthol with aromatic aldehydes and acetamide or thioacetamide in the presence of melamine-Br₃ under solvent-free conditions. There are several advantages to this reaction, including high yields, short reaction time, and high catalytic efficiency.

关键词: Multi-component reaction, Amidoalkyl naphthol, Tribromo-melamine, Solvent-free, One-pot

Abstract:

Key words: Multi-component reaction, Amidoalkyl naphthol, Tribromo-melamine, Solvent-free, One-pot

Arash Ghorbani-Choghamarani, Shima Rashidimoghadam. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1024-1029.

Arash Ghorbani-Choghamarani, Shima Rashidimoghadam. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions[J]. Chinese Journal of Catalysis, 2014, 35(7): 1024-1029.

×
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(14)60029-2

https://www.cjcatal.com/CN/Y2014/V35/I7/1024

参考文献

[1] Wang Y F, Izawa T, Kobayashi S, Ohno M. J Am Chem Soc, 1982, 104: 6465
[2] Knapp S. Chem Rev, 1995, 95: 1859
[3] Shen A Y, Chen C L, Lin C I. Chin J Physiol, 1992, 35: 45
[4] Szatmári I, Fülöp F. Curr Org Synth, 2004, 1: 155
[5] Shen A Y, Tsai C T, Chen C L. Eur J Med Chem, 1999, 34: 877
[6] Zhu X Y, Lee Y R, Kim S H. Bull Korean Chem Soc, 2012, 33: 2799
[7] Nagawade R R, Shinde D B. Chin J Chem, 2007, 25: 1710
[8] Patil S B, Singh P R, Surpur M P, Samant S D. Ultrason Sonochem, 2007, 14: 515
[9] Selvam N P, Perumal P T. Tetrahedron Lett, 2006, 47: 7481
[10] Rashinkar G, Salunkhe R. J Mol Catal A, 2010, 316: 146
[11] Wang M, Liang Y, Zhang T T, Gao J J. Chin Chem Lett, 2012, 23: 65
[12] Nagarapu L, Baseeruddin M, Apuri S, Kantevari S. Catal Commun, 2007, 8: 1729
[13] Hong M, Cai C, Yi W B. Chin Chem Lett, 2011, 22: 322
[14] Dorehgiraee A, Khabazzadeh H, Saidi K. Arkivoc, 2009, (7): 303
[15] Kumar A, Rao M S, Ahmad I, Khungar B. Can J Chem, 2009, 87: 714
[16] Shaterian H R, Yarahmadi H, Ghashang M. Bioorg Med Chem Lett, 2008, 18: 788
[17] Kantevari S, Vuppalapati S V N, Nagarapu L. Catal Commun, 2007, 8: 1857
[18] Khodaei M M, Khosropour A R, Moghanian H. Synlett, 2006: 916
[19] Supale A R, Gokavi G S. J Chem Sci, 2010, 122: 189
[20] Mistry S R, Joshi R S, Maheria K C. J Chem Sci, 2011, 123: 427
[21] Zhang P, Zhang Z H. Monatsh Chem, 2009, 140: 199
[22] Das B, Laxminarayana K, Ravikanth B, Rao B R. J Mol Catal A, 2007, 261: 180
[23] Khaksar S, Najafi R, Ostad S M, Tajbakhsh M. World Appl Sci J, 2012, 20: 656
[24] Kiasat A R, Mouradzadegun A, Saghanezhad S J. Chin J Catal (催化学报), 2013, 34: 1861
[25] Wu L Q. Eur J Chem, 2012, 9: 1035
[26] Ghorbani-Choghamarani A, Zolfigol M A, Hajjami M, Jafari S. J Chin Chem Soc, 2008, 55: 1208
[27] Zare A, Hasaninejad A, Rostami E, Moosavi-Zare A R, Pishahang N, Roshankar M, Khedri F, Khedri M. Eur J Chem, 2010, 7: 1162
[28] Zolfigol M A, Ghorbani-Vaghei R, Mallakpour S, Chehardoli G, Ghorbani-Choghamarani A, Yazdi A H. Synthesis, 2006: 1631
[29] Ghorbani-Choghamarani A, Amani K, Zolfigol M A, Hajjami M, Ayazi-Nasrabadi R. J Chin Chem Soc, 2009, 56: 255
[30] Liu Y L, Shi T D, Zhou F, Zhao X L, Wang X, Zhou J. Org Lett, 2011, 13: 3826
[31] Liu Y L, Zeng X P, Zhou J. Chem Asian J, 2012, 7: 1759
[32] Liu Y L, Zhou J. Chem Commun, 2013, 49: 4421

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions

One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions

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 15

编辑推荐

Metrics

[1]	Mahmoud. Abd, El Aleem. Ali, Ali. El-Remaily. Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-componentreaction[J]. 催化学报, 2015, 36(7): 1124-1130.
[2]	Abdol R. Hajipour, Hirbod Karimi, Afshin Koohi. Selective oxidation of alcohols over nickel zirconium phosphate[J]. 催化学报, 2015, 36(7): 1109-1116.
[3]	Nader Ghaffari Khaligh, Sharifah Bee Abd Hamid. 4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for the synthesis of pyrano[4, 3-b]pyran derivatives using thermal and ultrasonic irradiation[J]. 催化学报, 2015, 36(5): 728-733.
[4]	Hossein Naeimi, Hossein Foroughi. Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions[J]. 催化学报, 2015, 36(5): 734-741.
[5]	Abdol R. Hajipour, Hirbod Karimi, Amir Masti. Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate[J]. 催化学报, 2015, 36(4): 595-602.
[6]	Nader Ghaffari Khaligh. One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1’-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst[J]. 催化学报, 2014, 35(9): 1497-1503.
[7]	Bahador Karami, Mahtab Kiani, Mohsen Ahmad Hoseini. In(OTf)₃ as a powerful and recyclable catalyst for Pechmann condensation without solvent[J]. 催化学报, 2014, 35(7): 1206-1211.
[8]	Nader Ghaffari Khaligh, Parisa Ghods Ghasem-Abadi. N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate as a novel, efficient, and reusable solid acid catalyst for acylation under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1126-1135.
[9]	Nader Ghaffari Khaligh. Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst[J]. 催化学报, 2014, 35(7): 1036-1042.
[10]	Abolghasem Davoodnia, Maryam Khashi, Niloofar Tavakoli-Hoseini. Cerium (IV) sulfate：A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1054-1058.
[11]	Abolghasem Davoodnia, Rahil Mahjoobin, Niloofar Tavakoli-Hoseini. A facile, green, one-pot synthesis of amidoalkyl naphthols under solvent-free conditions catalyzed by a carbon-based solid acid[J]. 催化学报, 2014, 35(4): 490-495.
[12]	Nader Ghaffari Khaligh. Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate[J]. 催化学报, 2014, 35(4): 474-480.
[13]	Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Omid Khaledian, Vahid Khakyzadeh. Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts[J]. 催化学报, 2014, 35(4): 573-578.
[14]	Ali Keivanloo, Mahdi Mirzaee, Mohammad Bakherad, Atena Soozani. Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions[J]. 催化学报, 2014, 35(3): 362-367.
[15]	Saeed Farhadi, Kosar Jahanara. ZnAl₂O₄@SiO₂ nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions[J]. 催化学报, 2014, 35(3): 368-375.