Uncatalyzed, green aza-Michael addition of amines to dimethyl maleate

Tetrahedron

Volumn 70, Issue 37, 2014, Pages 6607-6612

  Bosica, Giovanna ^a   Debono, Anthony John ^a  

^a UNIVERSITY OF MALTA   (Malta)

Author keywords

aza Michael reaction; Catalyst free; Dimethyl maleate; Mono adduct; Solvent free

Indexed keywords

ALIPHATIC AMINE; DIMETHYL MALEATE; MALEIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME;

EID: 84949115568     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.06.124     Document Type: Article

References (84)

1. K. Tanaka Solvent-free Organic Synthesis 2003 Wiley-VCH Weinheim, Germany
2. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025 1074
3. B.C. Ranu, S.S. Dey, and A. Hajra ARKIVOC 7 2002 76 81
4. J.H. Clark Chemistry of Waste Minimisation 1995 Chapman and Hall London, UK
5. M. Poliakoff, J.M. Fitzpatrick, T.R. Farren, and P.T. Anastas Science 297 2002 807 810
6. A.Y. Rulev Russ. Chem. Rev. 80 2011 197 218
7. M.E. Jung B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford, UK 1
8. P. Perlmutter Conjugate Addition Reactions in Organic Synthesis 1992 Pergamon Oxford, UK 114
9. A. Harrison-Marchand, I. Chataigner, and J. Maddaluno Science of Synthesis Vol. 26 2005 Georg Thieme New York, NY 1225
10. G. Cardillo, and C. Tomassini Chem. Soc. Rev. 25 1996 117 128
11. J.S. Carey, D. Laffan, C. Thomson, and M.T. Williams Org. Biomol. Chem. 4 2006 2337 2347
12. R.W. Dugger, J.A. Ragan, and D.H. Brown Ripin Org. Process Res. Dev. 9 2005 253 258
13. S.E. Denmark, D.C. Forbes, D.S. Hays, J.S. De Pue, and R.G. Wilde J. Org. Chem. 60 1995 1391 1407
14. A.Y. Rulev, N. Yenil, A. Pesquet, H. Oulyadi, and J. Maddaluno Tetrahedron 62 2006 5411 5416
15. B.D. Mather, K. Viswanathan, K.M. Miller, and T.E. Long Prog. Polym. Sci. 31 2006 487 531
16. P.R. Krishna, A. Sreeshailam, and R. Srinivas Tetrahedron 65 2009 9657 9672
17. D. Pletsas, E.A.E. Garelnabi, L. Li, R.M. Phillips, and R.T. Wheelhouse J. Med. Chem. 56 2013 7120 7132
18. N.I. Georgiev, and V.B. Bojinov Dyes Pigm. 89 2010 249 256
19. Z. Amara, J. Caron, and D. Joseph Nat. Prod. Rep. 30 2013 1211 1225
20. E. Reyes, M. Fernandez, U. Uria, J.L. Vicario, D. Badia, and L. Carillo Curr. Org. Chem. 16 2012 521 546
21. A. Moyano, and R. Rios Chem. Rev. 111 2011 4703 4832
22. D. Enders, C. Wang, and J.X. Liebich Chem. - Eur. J. 15 2009 11058 11076
23. Y. Hamashima Chem. Pharm. Bull. 54 2006 1351 1364
24. L.-W. Xu, and C.-G. Xia Eur. J. Org. Chem. 4 2005 633 639
25. M.P. Sibi, and S. Manyem Tetrahedron 56 2000 8033 8061
26. N. Azizi, and M.R. Saidi Tetrahedron 60 2004 383 387
27. P.W.H. Chan, I.F. Cottrel, and M.G. Moloney Tetrahedron Lett. 38 1997 5891 5894
28. N.S. Shaikh, V.H. Deshpande, and A.V. Bedekar Tetrahedron 57 2001 9045 9048
29. G. Jenner Tetrahedron Lett. 36 1995 233 236
30. S. Kobayashi, K. Karumoto, and M. Sugiura Org. Lett. 4 2002 1319 1322
31. I. Reboule, R. Gil, and J. Collin Tetrahedron Lett. 46 2005 7761 7764
32. X. Hou, H. Hemit, J. Yong, L. Nie, and H. Aisa Synth. Commun. 40 2010 973 979
33. T. Wei, M. Hua, H. Shi, Y. Liu, and Y. Zhang J. Chem. Res. 2010 452 454
34. J.S. Yadav, A.R. Reddy, Y.G. Rao, A.V. Narsaiah, and B.V.S. Reddy Synthesis 2007 3447 3450
35. A.T. Khan, T. Parvin, S. Gazi, and L. Choudhury Tetrahedron Lett. 48 2007 3805 3808
36. Z. Duan, X. Xuan, T. Li, C. Yang, and Y. Wu Tetrahedron Lett. 47 2006 5433 5436
37. R. Varala, N. Sreelatha, and S.R. Adapa Synlett 2006 1549 1553
38. G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massacesi, and E. Torregiani J. Org. Chem. 70 2005 169 174
39. C. Mukherjee, and A. Misra Lett. Org. Chem. 4 2007 54 59
40. Y. Wang, Y.-Q. Yuan, and S.-R. Guo Molecules 14 2009 4779 4789
41. M.R. Saidi, Y. Pourshojaei, and F. Aryanasab Synth. Commun. 39 2009 1109 1119
42. R. Pal, T. Sarkar, and S. Khasnobis ARKIVOC i 2012 570 609
43. B. Das, and N. Chowdhury J. Mol. Catal. A Chem. 263 2007 212 215
44. V.R. Choudhary, D.K. Dumbre, and S.K. Patil RSC Adv. 2 2012 7061 7065
45. X.-X. Mao, Y.-M. Shen, J. Wang, and Q.-H. Xia Kinet. Catal. 52 2011 525 528
46. M. Vijender, P. Kishore, and B. Satyanarayana Synth. Commun. 37 2007 589 592
47. I.P. Beletskaya, E.A. Tarasenko, A.R. Khokhlov, and V.S. Tyurin Russ. J. Org. Chem. 46 2010 461 467
48. V. Polshettiwar, and R.S. Varma Tetrahedron Lett. 48 2007 8735 8738
49. D. Kumar, G. Patel, B.G. Mishra, and R.S. Varma Tetrahedron Lett. 49 2008 6974 6976
50. J.-M. Xu, Q. Wu, Q.-Y. Zhang, F. Zhang, and X.-F. Lin Eur. J. Org. Chem. 2007 1798 1802
51. A. Ying, M. Zheng, H. Xu, F. Qiu, and C. Ge Res. Chem. Intermed. 37 2011 883 890
52. A.-G. Ying, L.-M. Wang, H.-X. Deng, J.-H. Chen, X.-Z. Chen, and W.-D. Ye ARKIVOC xi 2009 288 298
53. X. Chen, X. Li, H. Song, Y. Qian, and F. Wang Tetrahedron Lett. 52 2011 3588 3591
54. B.C. Ranu, and S. Banerjee Tetrahedron Lett. 48 2007 141 143
55. V.B. Labade, S.S. Pawar, and M.S. Shingare Monatsh. Chem. 142 2011 1055 1059
56. E.V. Matveeva, P.V. Petrovskii, Z.S. Klemenkova, N.A. Bondarenko, and I.L. Odinets C. R. Chim. 13 2010 964 970
57. M. Saikia, D. Kakati, M.S. Joseph, and J.C. Sarma Lett. Org. Chem. 6 2009 654 658
58. X. Ai, X. Wang, J.-M. Liu, Z.-M. Ge, T.-M. Cheng, and R.-T. Li Tetrahedron 66 2010 5373 5377
59. J. Nath, and M.K. Chaudhuri Catal. Lett. 133 2009 388 393
60. F. Medina, C. Michon, and F. Agbossou-Niedercorn C. R. Chim. 16 2013 311 317
61. R. Ballini, S. Gabrielli, and A. Palmieri Curr. Org. Chem. 14 2010 65 83
62. R. Ballini, N.A. Bazán, G. Bosica, and A. Plamieri Tetrahedron Lett. 49 2008 3865 3867
63. R. Ballini, and G. Bosica Liebigs Ann. Chem. 1996 2087 2089
64. R. Ballini, G. Bosica, D. Fiorini, and P. Righi Synthesis 2002 681 685
65. R. Ballini, G. Bosica, A. Palmieri, M. Petrini, and C. Pierantozzi Tetrahedron 59 2003 7283 7289
66. R. Ballini, G. Bosica, A. Masè, and M. Petrini Eur. J. Org. Chem. 2000 2927 2931
67. R. Ballini, and G. Bosica Tetrahedron 51 1995 4213 4222
68. R. Ballini, G. Bosica, M. Damiani, and P. Righi Tetrahedron 55 1999 13451 13456
69. R. Ballini, L. Barboni, G. Bosica, D. Fiorini, and A. Palmieri Pure Appl. Chem. 78 2006 1857 1866
70. R. Ballini, and A. Palmieri Adv. Synth. Catal. 348 2006 1154 1156
71. X. Liang, Y. Wang, G. Gong, and J. Yang Catal. Commun. 10 2008 281 284
72. M. Boros, J. Kökösi, J. Vámos, I. Kövesdi, and B. Noszál Amino Acids 33 2007 709 717
73. M. Pfau Bull. Soc. Chim. Fr. 1967 1117 1125
74. P. Zaderenko, M.C. López, and P. Ballesteros J. Org. Chem. 61 1996 6825 6828
75. Y. Okada, T. Banno, K. Toshima, and S. Matsumura J. Oleo Sci. 58 2009 519 528
76. T. Straub, and A.M.P. Koskinen Polym. Prepr. 46 2005 687
77. G. Bosica, J. Spiteri, and C. Borg Tetrahedron 70 2014 2449 2454
78. J.W. Davis, and A. Furst Anal. Chem. 40 1968 1910 1912
79. C. Faderl, G. Kachkovskyi, O. Reiser, and G. Kachkovskyi Adv. Synth. Catal. 355 2013 2240 2248
80. Y. Nakajima, J. Oda, and Y. Inouye Agric. Biol. Chem. 39 1975 2065 2068
81. R.T. Coutts, J.W. Hubbard, K.K. Midha, and K. Prasad J. Pharm. Sci. 60 1971 28 33
82. J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah Chem. Lett. 32 2003 988 989
83. M.L. Gay, P. Molton, and C. Ponnamperuma Org. Mass Spectrom. 9 1974 1124 1126
84. T.T. Denton, A.S. Joyce, and D.E. Kiely J. Org. Chem. 72 2007 4997 5000