Potassium phthalimide-N-oxyl: A novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water

Tetrahedron

Volumn 69, Issue 3, 2013, Pages 1074-1085

  Dekamin, Mohammad G ^a   Eslami, Mohammad ^a   Maleki, Ali ^a  

^a IRAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Iran)

Author keywords

2 Amino 4H chromene; Green chemistry; Multi component reactions (MCRs); Potassium phthalimide N oxyl (POPINO); Transition metal free catalysis

Indexed keywords

2 AMINO 4H CHROMENE DERIVATIVE; ALDEHYDE; CHROMENE DERIVATIVE; ETHYL CYANOACETATE; MALONONITRILE; PHTHALIMIDE DERIVATIVE; POTASSIUM PHTHALIMIDE N OXYL; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; ONE POT THREE COMPONENT SYNTHESIS; PRIORITY JOURNAL;

EID: 84871629451     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.068     Document Type: Article

References (93)

1. J. Zhu, and H. Bienayme Multicomponent Reactions 2005 Wiely-VCH Weinheim
2. B. Ganem Acc. Chem. Res. 42 2009 463 472
3. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3169 3210
4. A. Shaabani, A. Maleki, A.H. Rezayan, and A. Sarvary J. Mol. Divers. 15 2011 41 68
5. C. Altug, A.K. Burnett, E. Caner, Y. Dürüst, M.C. Elliott, R.P.J. Glanville, C. Guy, and A.D. Westwell Tetrahedron 67 2011 9522 9528
6. M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, P.A. Belyakov, and A.O. Chizhov Tetrahedron 66 2010 4043 4048
7. M.G. Dekamin, and Z. Mokhtari Tetrahedron 68 2012 922 930
8. M.G. Dekamin, Z. Mokhtari, and Z. Karimi Sci. Iran. Trans. C: Chem. Chem. Eng. 18 2011 1356 1364
9. Z. Dong, X. Liu, J. Feng, M. Wang, L. Lin, and X. Feng Eur. J. Org. Chem. 1 2011 137 142
10. L. Moafi, S. Ahadi, and A. Bazgir Tetrahedron Lett. 51 2010 6270 6274
11. L. Alvey, S. Prado, V. Huteau, B. Saint-Jonis, S. Michel, M. Koch, S.T. Cole, F. Tillequin, and Y.L. Janin Bioorg. Med. Chem. 16 2008 8264 8272
12. T. Symeonidis, M. Chamilos, D.J. Hadjipavlou-Litina, M. Kallitsakis, and K.E. Litinas Bioorg. Med. Lett. 19 2009 1139 1142
13. T. Narender, Shweta, and S. Gupta Bioorg. Med. Chem. Lett. 14 2004 3913 3916
14. L. Lakshmi, K. Pandey, A. Kapil, N. Singh, M. Samant, and A. Dube Phytomedicine 14 2007 36 42
15. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, and S. Kapur Eur. J. Med. Chem. 44 2009 3805 3809
16. A.M. El-Agrody, M.H. El-Hakium, M.S. Abd El-Latif, A.H. Fekry, E.S.M. El-Sayed, and K.A. El-Gareab Acta Pharm. 50 2000 111 120
17. M.C. Yimdjo, A.G. Azebaze, A.E. Nkengfack, A. Michele Meyer, B. Bodo, and Z.T. Fomum Phytochemistry 65 2004 2789 2795
18. Z.Q. Xu, K. Pupek, W.J. Suling, L. Enache, and M.T. Flavin Bioorg. Med. Chem. Lett. 14 2006 4610 4626
19. L. Alvey, S. Prado, B. Saint-Joanis, S. Michel, M. Koch, S.T. Cole, F. Tillequin, and Y.L. Janin Eur. J. Med. Chem. 44 2009 2497 2505
20. V.K. Tandon, M. Vaisha, S. Jain, D.S. Bhakuni, and R.C. Srimal Indian J. Pharm. Sci. 53 1991 22 23
21. L. Bonsignore, G. Loy, D. Secci, and A. Calignano Eur. J. Med. Chem. 28 1993 517 520
22. A.G. Martinez, and L.J. Marco Bioorg. Med. Chem. Lett. 7 1997 3165 3170
23. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, and J.W. Pryor Cancer Res. 35 1975 3750 3754
24. Y. Gao, W. Yang, and D.M. Du Tetrahedron: Asymmetry 23 2012 339 344
25. G.A. Reynolds, and K.H. Drexhage Opt. Commun. 13 1975 222 225
26. H. Zollinger Color Chemistry 3rd ed 2003 Verlag Helvetica Chimica Acta Zurikh and Wiley-VCH: Weinheim
27. E.R. Bissell, A.R. Mitchell, and R.E. Smith J. Org. Chem. 45 1980 2283 2287
28. G.P. Ellis A. Weissberger, E.C. Taylor, The Chemistry of Heterocyclic of Compounds. Chromenes, Harmones and Chromones 1977 John Wiley New York, NY 11 13 Chapter II
29. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, and F.M.A.A. El-Taweel Heterocycles 26 1987 903 907
30. R. Ballini, G. Bosica, L.,M. Conforti, R. Maggi, A. Mazzacani, P. Righi, and G. Sartori Tetrahedron 57 2001 1395 1398
31. T.S. Jin, J.C. Xiao, S.,J. Wang, and T.S. Li Ultrason. Sonochem. 11 2004 393 397
32. T.S. Jin, J.S. Zhang, L.B. Liu, A.Q. Wang, and T.S. Li Synth. Commun. 36 2006 2009 2015
33. T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, and X.R. Song Synlett 2003 2001 2004
34. D.Q. Shi, S.I. Zhang, Q.Y. Zhuang, and X.S. Wang Chin. J. Org. Chem. 23 2003 1419 1421
35. C. Lu, X.J. Huang, Y.Q. Li, M.Y. Zhou, and W. Zheng Monatsh. Chem. 140 2009 45 47
36. L. Chen, Y.Q. Li, X.J. Huang, and W.J. Zheng Heteroat. Chem. 20 2009 91 94
37. M. Al-Matar, K.D. Khalil, H. Meier, H. Kolshorn, and M.H. Elnagdi Arkivoc xvi 2008 288 301
38. R. Ballini, F. Bigi, M.L. Conforti, D.D. Santis, R. Maggi, G. Oppici, and G. Sartori Catal. Today 60 2000 305 309
39. Z. Zhou, F. Yang, L. Wu, and A. Zhang Chem. Sci. Trans. 1 2012 57 60
40. M. Kidwai, S. Saxena, M.K. Rahman Khan, and S.S. Thukral Bioorg. Med. Chem. Lett. 15 2005 4295 4298
41. M.R. Naimi-jamal, S. Mashkouri, and A. Sharifi Mol. Divers. 14 2010 473 477
42. D. Kumar, V.B. Reddy, G.B. Mishra, R.K. Rann, M.N. Nadagouda, and R.S. Varma Tetrahedron 63 2007 3093 3097
43. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, and F.F. Bamoharram Bioorg. Med. Chem. Lett. 17 2007 4262 4265
44. M.P. Surpur, S. Kshirsagar, and S. Samant Tetrahedron Lett. 50 2009 719 722
45. B.S. Kumar, N. Shrinvasulu, R.H. Udupi, B. Rajitha, Y.T. Reddy, P.N. Reddy, and P.S. Kumar J. Heterocycl. Chem. 43 2006 1691 1693
46. M.M. Heravi, B. Baghernejad, and H.A. Oskooie J. Chin. Chem. Soc. 55 2008 659 662
47. J.F. Zhou, S.J. Tu, Y. Gao, and M. Ji Chin. J. Org. Chem. 21 2001 742 745
48. K. Rad-Moghadam, and L. Yoseftabar-Miri Tetrahedron 67 2011 5693 5699
49. Y. Peng, and G. Song Catal. Commun. 8 2007 111 114
50. M.J. Khurana, B. Nand, and P. Saluja Tetrahedron 66 2010 5637 5641
51. D.S. Raghuvanshi, and K.N. Singh Arkivoc 10 2010 305 317
52. W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. gourdeau, B. Tseng, J. Drewe, and S.X. Cai Bioorg. Med. Chem. Lett. 15 2005 4745 4751
53. M.G. Dekamin, F.M. Moghaddam, H. Saiedian, and S. Mallakpour Monatsh. Chem. 137 2006 1591 1595
54. M.G. Dekamin, K. Varmira, M. Farahmand, S. Sagheb-Asl, and Z. Karimi Catal. Commun. 12 2010 226 230
55. M.G. Dekamin, S. Javanshir, M.R. Naimi-Jamal, R. Hekmatshoar, and J. Mokhtari J. Mol. Catal. A: Chem. 283 2008 29 32
56. M.G. Dekamin, J. Mokhtari, and M.R. Naimi-Jamal Catal. Commun. 10 2009 582 585
57. M.G. Dekamin, N. Yazdaninia, J. Mokhtari, and M.R. Naimi-Jamal J. Iran. Chem. Soc. 8 2011 537 544
58. R. Breslow M. Lindstrom, Organic Reactions in Water 2007 Blackwell Oxford 1 28
59. R. Breslow, and D.C. Rideout J. Am. Chem. Soc. 102 1980 7816 7817
60. R. Breslow Acc. Chem. Res. 24 1991 159 164
61. M. Kazemzad, A.A. Yuzbashi, S. Balalaie, and M. Bararjanian Synth. React. Inorg. M. 41 2011 1182 1187
62. D. Fang, H.B. Zhang, and Z.L. Liu J. Heterocycl. Chem. 47 2010 63 67
63. S. Balalaie, M. Bararjanian, A.M. Amani, and B. Movassagh Synlett 2006 263 266
64. S. Gao, C.H. Tsai, C. Tseng, and C.F. Yao Tetrahedron 64 2008 9143 9149
65. R. Liangce, L. Xiaoyue, W. Haiying, S. Daqing, T. Shujiang, and Z. Oiya Synth. Commun. 36 2006 2363 2369
66. A. Patra, and T. Mahapatra J. Chem. Res., Synop. 34 2010 689 693
67. T.A. Khan, M. Lal, S. Ali, and M.M. Khan Tetrahedron Lett. 52 2011 5327 5332
68. L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, and B. Liu J. Fluorine Chem. 127 2006 97 100
69. S. Gowravaram, K. Arundhathi, K.,B.S. Sudhakar, and J.S. Yadav Synth. Commun. 39 2009 433 442
70. M. Hong, and C. Cai J. Chem. Res., Synop. 34 2010 568 570
71. V.D. Dyachenko, and A.N. Chernega Russ. J. Org. Chem. 42 2006 567 576
72. Y. Yi, G. Hongyun, and L. Xiaojun J. Heterocycl. Chem. 48 2011 1264 1268
73. M. Khodeir, F. El-Taweel, and A. Elagamey Pharmazie 47 1992 486 487
74. M.M. Heravi, M. Zakeri, and N. Mohammadi Chin. J. Chem. 29 2011 1163 1166
75. S. Abdolmohammadi, and S. Balalaie Tetrahedron Lett. 48 2007 3299 3303
76. S.M. Al-Mousawi, Y.M. Elkholy, M.A. Mohammad, and M.H. Elnagdi Org. Prep. Proced. Int. 31 1999 305 313
77. H.R. Shaterian, and M. Honarmand Synth. Commun. 41 2011 3573 3581
78. H. Mehrabi, and M. Kazemi-Mireki Chin. Chem. Lett. 22 2011 1419 1422
79. W. Hong-juan, L. Jie, and Z. Zhan-Hui Monatsh. Chem. 141 2010 1107 1112
80. T. Shujiang, J. Hong, F. Fang, F. Youjian, Z. Songlei, L. Tuanjie, Z. Xiaojing, and S. Daqing J. Chem. Res., Synop. 6 2004 396 398
81. M.P. Goncharenko, and Y.A. Sharanin Russ. J. Org. Chem. 29 1993 1118 1129
82. H. Eshghi, S. Damavandi, and G.H. Zohuri Synth. React. Inorg. Met. 41 2011 1067 1073
83. A.F. Mahmoud, E.L. Abd, F. Fathy, and A.M. Ahmed Chin. J. Chem. 28 2010 91 96
84. S. Makarem, A.A. Mohammadi, and A.R. Fakhari Tetrahedron Lett. 49 2008 7194 7196
85. A.G.A. Elagamey, and F.M.A.A. El-Taweel Indian J. Chem. B 29 1990 885 886
86. R.A. Mekheimer, and K.U. Sadek J. Heterocycl. Chem. 46 2009 149 151
87. A. Patra, and T. Mahapatra J. Chem. Res. 2008 405 408
88. K. Gong, H.L. Wang, D. Fang, and Z.L. Liu Catal. Commun. 9 2008 650 653
89. W.B. Sun, P. Zhang, J. Fan, S.H. Chen, and Z.H. Zhang Synth. Commun. 40 2010 587 594
90. B. Boumoud, A.A. Yahiaoui, T. Boumoud, and A. Debache J. Chem. Pharm. Res. 4 2012 795 799
91. M. Shi, J. Mou, Q. Zhuang, and X. Wang J. Chem. Res. 2004 821 823
92. X.Z. Lian, Y. Huang, Y.Q. Li, and W.J. Zheng Monatsh. Chem. 139 2008 129 131
93. D. Tahmassebi, A.B. Jessica, and S. Binz Catal. Commun. 41 2011 2701 2711