Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

Tetrahedron

Volumn 69, Issue 1, 2013, Pages 212-218

  Khazaei, Ardeshir ^a   Zolfigol, Mohammad Ali ^a   Moosavi Zare, Ahmad Reza ^a   Abi, Fereshteh ^b   Zare, Abdolkarim ^b   Kaveh, Hamideh ^b   Khakyzadeh, Vahid ^a   Kazem Rostami, Masoud ^a   Parhami, Abolfath ^b   Torabi Monfared, Hossein ^b  

^a BU ALI SINA UNIVERSITY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

1 Amido alkyl 2 naphthol; 1 Carbamato alkyl 2 naphthol; 1 Thioamido alkyl 2 naphthol; Multi component condensation; Solvent free; Trityl chloride

Indexed keywords

2 NAPHTHOL; ACETAMIDE; ALDEHYDE; AMIDE; BENZAMIDE; CARBAMIC ACID; CATION; CHLORIDE; NICOTINAMIDE; SOLVENT; THIOACETAMIDE; THIOAMIDE; TRITYL CHLORIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 84870060880     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.10.042     Document Type: Article

References (45)

1. A.Y. Shen, C.T. Tsai, and C.L. Chen Eur. J. Med. Chem. 34 1999 877 882
2. T. Dingermann, D. Steinhilber, and G. Folkers Molecular Biology in Medicinal Chemistry 2004 Wiley-VCH Weinheim
3. A.Y. Shen, C.L. Chen, and C.I. Lin Chin. J. Physiol. 35 1992 45 54
4. M. Damodiran, N.P. Selvam, and P.T. Perumal Tetrahedron Lett. 50 2009 5474-4578
5. T. Haneishi, T. Okazaki, T. Hata, C. Tamura, M. Nomura, A. Naito, I. Seki, and M. Arai J. Antibiot. 24 1971 797 799
6. K. Sasaki, Y. Kusakabe, and S. Esumi J. Antibiot. 25 1972 151 154
7. Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, and S. Shirato J. Antibiot. 25 1972 44 47
8. M.C. Wani, H.L. Taylor, and M.E. Wall J. Chem. Soc.; Chem. Commun. 1973 390 396
9. P.Y. Jonson, and R.B. Silver J. Heterocycl. Chem. 10 1973 1029 1030
10. S. Remillard, L.I. Rebhun, G.A. Howie, and S.M. Kupchan Science 189 1975 1002 1005
11. Urbański, T.; Ghrne, D.; Szczerek, I.; Modaski, M. Polish Patent 54, 007, 1967.
12. G.Y. Lesher, and A.R. Surrey J. Am. Chem. Soc. 77 1955 636 641
13. H.S. Mosher, M.B. Frankel, and M. Gregory J. Am. Chem. Soc. 75 1953 5326 5328
14. J.L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot, and M. Millan Bioorg. Med. Chem. Lett. 7 1997 881 886
15. H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna, S. Croft, H. Kendrick, V. Yardley, and G. Moyna Bioorg. Med. Chem. Lett. 11 2001 1851 1854
16. F. Benedini, G. Bertolini, R. Cereda, G. Doná, G. Gromo, S. Levi, J. Mizrahi, and A. Sala J. Med. Chem. 38 1995 130 136
17. R.D. Clark, J.M. Caroon, A.F. Kluge, D.B. Repke, A.P. Roszkowski, A.M. Strosberg, S. Baker, S.M. Bitter, and M.D. Okada J. Med. Chem. 26 1983 657 661
18. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, and T. Kuroki J. Med. Chem. 40 1997 105 111
19. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, and V. Khakyzadeh Appl. Catal. A: Gen. 400 2011 70 81
20. Z.-J. Quan, R.-G. Ren, Y.-X. Da, Z. Zhang, and X.-C. Wang Synth. Commun. 41 2011 3106 3116
21. F.F. Bamoharram, M.M. Heravi, M. Roshani, and M.J.S. Charkhi E- J. Chem. 8 2011 523 528
22. V.J. Rani, M. Suresh, P. Lavanya, K.V. Vani, B. Nagarjuna, and C.V. Rao Der Pharma Chem. 2 2010 224 227
23. N.S. Suryawanshi, and P. Jain Orient. J. Chem. 26 2010 1525 1529
24. Q. Zhang, J. Luo, and Y. Wei Green. Chem. 12 2010 2246 2254
25. K.S. Niralwad, B.B. Shingate, and M.S. Shingare Chin. Chem. Lett. 22 2011 551 554
26. M. Hong, C. Cai, and W.B. Yi Chin. Chem. Lett. 22 2011 322 325
27. B. Datta, and M.A. Pasha Ultrason. Sonochem. 18 2011 624 628
28. N.P. Selvam, and P.T. Perumal Tetrahedron Lett. 47 2006 7481 7483
29. H.R. Shaterian, H. Yarahmadi, and M. Ghashang Bioorg. Med. Chem. Lett. 18 2008 788 792
30. S.B. Patil, P.R. Singh, M.P. Surpur, and S.D. Samant Ultrason. Sonochem. 14 2007 515 518
31. G. Srihari, M. Nagaraju, and M.M. Murthy Helv. Chim. Acta 90 2007 1497 1504
32. D. Kundu, A. Majee, and A. Hajra Catal. Commun. 11 2010 1157 1159
33. H.R. Shaterian, A. Hosseinian, and M. Ghashang Tetrahedron Lett. 49 2008 5804 5806
34. M.M. Heravi, N. Tavakoli-Hoseini, and F.F. Bamoharram Green Chem. Lett. Rev. 3 2010 263 267
35. M. Dabiri, A.S. Delbari, and A. Bazgir Heterocycles 71 2007 543 548
36. A. Dondoni, and A. Massi Angew. Chem.; Int. Ed. 47 2008 4638 4660
37. S. Verma, L.S. Jain, and B. Sain Tetrahedron Lett. 51 2010 6897 6900
38. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, and A. Khalafi-Nezhad Catal. Commun. 20 2012 54 57
39. A. Khalafi-Nezhad, A. Parhami, A. Zare, A.R. Moosavi Zare, A. Hasaninejad, and F. Panahi Synthesis 2008 617 621
40. A. Khalafi-Nezhad, A. Parhami, A. Zare, A. Nasrollahi Shirazi, A.R. Moosavi Zare, and A. Hasaninejad Can. J. Chem. 86 2008 456 461
41. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, A. Parhami, and A. Khalafi-Nezhad Appl. Catal. A: Gen. 386 2010 179 187
42. M. Oikawa, H. Yoshizaki, and S. Kusumoto Synlett 1998 757 760
43. J. Wen-Qing, A. Li-Tao, and Z. Jian-Ping Chin. J. Chem. 26 2008 1697 1705
44. M. Wang, and Y. Liang Monatsh. Chem. 142 2011 153 157
45. J. Luo, and Q. Zhang Monatsh. Chem. 142 2011 923 930