Microwave-assisted selective and efficient synthesis of 1,3,5-triazinyl mono and bisureas

Tetrahedron

Volumn 70, Issue 9, 2014, Pages 1733-1739

  Ruiz Carretero, Amparo ^a   Ramírez, José Ramón ^a   Sánchez Migallón, Ana ^a   De La Hoz, Antonio ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Green chemistry; Hydrogen bonds; Microwave; Triazine; Ureas

Indexed keywords

1,3,5 TRIAZINE 2,4 DIAMINE; 1,3,5 TRIAZINYL BISUREA; 1,3,5 TRIAZINYL MONOUREA; HETEROCYCLIC COMPOUND; PHENYL ISOCYANATE; SOLVENT; TRIAZINE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; GREEN CHEMISTRY; HYDROGEN BOND; MICROWAVE ASSISTED SYNTHESIS; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION TIME;

EID: 84893777860     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.01.043     Document Type: Article

References (66)

1. A.F. Pozharskii, A.T. Soldatenkov, and A.R. Katrizky Heterocycles in Life and Society 1997 Wiley Chichester, West Sussex, UK
2. A.R. Katrizky, and A.F. Pozharskii Handbook of Heterocyclic Chemistry 2nd ed. 2000 Pergamon Oxford, UK
3. A. Venkatesan, C. Dehnhart, E. de los Santos, Z. Chen, O. Dos Santos, S. Ayral-Kaloustian, G. Khafidova, N. Brooijmans, R. Mallon, I. Hollander, L. Feldberg, J. Lucas, K. Yu, J. Gibbons, R. Abraham, I. Chaudhary, and T. Mansour J. Med. Chem. 53 2010 2636 2645
4. T.J. Mooibroek, and P. Gamez Inorg. Chim. Acta 360 2007 381 404
5. S. Yagai J. Photochem. Photobiol., C. 7 2006 164 182
6. S. Ren, D. Zeng, H. Zhong, Y. Wang, S. Qian, and Q. Fang J. Phys. Chem. B 114 2010 10374 10383
7. M.M. Rothmann, S. Haneder, E. Da Como, C. Lennartz, C. Schildknetch, and P. Strohriegl Chem. Mater. 22 2010 2403 2410
8. M. El-Sedik, N. Almonasy, M. Nepras, F. Bures, M. Dvorák, M. Michl, J. Cermák, and R. Hrdina Dyes Pigments 92 2012 1126 1131
9. H.K. Dambal, and C.V. Yelamaggad Tetrahedron Lett. 53 2012 186 190
10. D.E. Gómez, L. Fabbrizzi, M. Licchelli, and E. Monzani Org. Biomol. Chem. 3 2005 1495 1500
11. T. Gunnlaugsson, A.P. Davis, J.E. O'Brien, and M. Glynn Org. Biomol. Chem. 3 2005 48 56
12. A. Aldrey, A. Macías, R. Bastida, G. Zaragoza, G. Rama, and M. Vázquez López Org. Biomol. Chem. 10 2012 5379 5384
13. C. Lincheneau, R.M. Duke, and T. Gunnlaugsson Org. Biomol. Chem. 10 2012 6069 6073
14. M.B. Jiménez, V. Alcázar, R. Peláez, F. Sanz, Á.L. Fuentes de Arriba, and M.C. Caballero Org. Biomol. Chem. 10 2012 1181 1185
15. A.T. ten Cate, and R.P. Sijbesma Macromol. Rapid Commun. 23 2002 1094 1112
16. R. Custelcean Chem. Commun. 2008 295 307
17. L. Brunsveld, J.A.J.M. Vekemans, J.H.K.K. Hirschberg, R.P. Sijbesma, and E.W. Meijer Proc. Natl. Acad. Sci. U.S.A. 99 2002 4977 4982
18. P. Jonkheijm, P. van der Schoot, A.P.H.J. Schenning, and E.W. Meijer Science 313 2006 80 83
19. P. Jonkheijm, N. Stutzmann, Z. Chen, D.M. de Leeuw, E.W. Meijer, A.P.H.J. Schenning, and F. Würthner J. Am. Chem. Soc. 128 2006 9535 9540
20. S. Jensen, H. Früchtl, and C.J. Baddeley J. Am. Chem. Soc. 131 2009 16706 16713
21. K. Iro, and E. Ichikawa Bull. Chem. Soc. Jpn. 57 1984 2009 2010
22. H. Kooijman, A.L. Spek, F.H. Beijer, R.P. Sijbesma, and E.W. Meijer Acta Crystallogr. E59 2003 01546 01548
23. S.J. George, Ž. Tomović, M.M.J. Smulders, T.F.A. de Greef, P.E.L.G. Leclère, E.W. Meijer, and A.P.H.J. Schenning Angew. Chem., Int. Ed. 46 2007 8206 8211
24. M. Wolffs, S.J. George, Ž. Tomović, S.C.J. Meskers, A.P.H.J. Schenning, and E.W. Meijer Angew. Chem., Int. Ed. 46 2007 8203 8205
25. M. Wolffs, M. Malisauskas, I. De Cat, Z. Tomović, J. van Herrikhuyzen, C.M.A. Leenders, E.J. Spadafora, B. Grévin, S. De Feyter, E.W. Meijer, A.P.H.J. Schenning, and P. Leclère Chem. Commun. 2011 9333 9335
26. J.E. Herweh, and W.Y. Whitmore J. Chem. Eng. Data 15 1970 593 595
27. A.P.H.J. Schenning, P. Jonkheijm, E. Peeters, and E.W. Meijer J. Am. Chem. Soc. 123 2001 409 416
28. Tao, C.; Han, H.; Sun, X.; Desai, N. WO2010/144404 A1.
29. Sattigeri, V. J.; Salman, M.; Narayanan, R.; Seth, S.; Sarin, S.; Ray, A.; Dastidar, S. G. US 2006/0004005 A1.
30. H. Kitayima, T. Imanaka, and T. Yamamoto Yuki Gosei Kagaku Kyokaishi 32 1974 723 726
31. E.F.J. Duynstee, and Th. A. Verrkamp Recl. Trav. Chim. Pays-Bas 81 1962 241 254
32. de la Hoz, A.; Sánchez-Migallón, A. Unpublished results.
33. C.-J. Li, and P.T. Anastas Chem. Soc. Rev. 41 2012 1413 1414
34. C. Jiménez-González, D.J.C. Constable, and C.S. Ponder Chem. Soc. Rev. 41 2012 1485 1498
35. W.J.W. Watson Green Chem. 14 2012 251 259
36. A. de la Hoz, A. Díaz-Ortiz, M. Moral, J. Elguero, C. Foces, and A. Sánchez-Migallón Tetrahedron 62 2006 5868 5874
37. M. Moral, A. Ruiz, A. Moreno, A. Díaz-Ortiz, I. López-Solera, A. de la Hoz, and A. Sánchez-Migallón Tetrahedron 66 2010 121 127
38. R.B.N. Baig, and R.S. Varma Chem. Soc. Rev. 41 2012 1559 1584
39. rd ed. 2012 Wiley-VCH Weinheim
40. nd ed. 2012 Wiley-VCH Weinheim, Germany
41. J.P. Tierney, and P. Lidström Microwave-assisted Organic Synthesis 2005 Blackwell Oxford, UK
42. C.O. Kappe, D. Dallinger, and S.S. Murphree Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols 2009 Wiley-VCH Weinheim, Germany
43. N. Leadbeater Microwave Heating as a Tool for Sustainable Chemistry 2010 CRC Boca Raton, FL
44. A. Sharma, P. Appukkuttanab, and E. Van der Eycken Chem. Commun. 2012 1623 1637
45. A. Dastan, A. Kulkarnia, and B. Török Green Chem. 14 2012 17 37
46. P.T. Anastas, and J.C. Warner Green Chemistry: Theory and Practice 1998 Oxford University Press Oxford. UK
47. P.J. Dunn Chem. Soc. Rev. 41 2012 1452 1461
48. T. Laird Org. Process Res. Dev. 16 2012 1 2
49. J. Alcázar, A. de la Hoz, A. Díaz-Ortiz, J.R. Carrillo, M.A. Herrero, A. Fontana, and J.M. Muñoz Comb. Chem. High Throughput Screen. 14 2011 109 116
50. A. Díaz-Ortiz, J. Elguero, A. de la Hoz, A. Moreno, A. Sánchez-Migallón, C. Foces-Foces, M.C. Mateo, and G. Valiente New J. Chem. 28 2004 952 958
51. I. Ghiviriga, and D.C. Oniciu Chem. Commun. 2002 2718 2719
52. A. Díaz-Ortiz, J. Elguero, C. Foces-Foces, A. de la Hoz, A. Moreno, S. Moreno, A. Sánchez-Migallón, and G. Valiente Org. Biomol. Chem. 1 2003 4451 4457
53. H.E. Birkett, J.C. Cherryman, A.M. Chippendale, J.S.O. Evans, R.K. Harris, M. James, I.J. King, and G.J. McPherson Magn. Reson. Chem. 41 2003 324 336
54. J. Sandström Dynamic NMR Spectroscopy 1982 Academic New York, NY
55. W.L. Jorgensen, and J. Pranata J. Am. Chem. Soc. 112 1990 2008 2010
56. J. Pranata, S.G. Wierschke, and W.L. Jorgensen J. Am. Chem. Soc. 113 1991 2810 2819
57. F.H. Beijer, R.P. Sijbesma, H. Kooijman, A.L. Spek, and E.W. Meijer J. Am. Chem. Soc. 120 1998 6761 6769
58. R.P. Sijbesma, and E.W. Meijer Chem. Commun. 2003 5 16
59. E.W. Meijer, and A.R.A. Palmans Angew. Chem., Int. Ed. 46 2007 8948 8968
60. M.H.C.L. Dressen, B.H.P. van de Kruijs, J. Meuldijk, J.A.J.M. Vekemans, and L.A. Hulshof Org. Process Res. Dev. 15 2011 140 147
61. M.H.C.L. Dressen, B.H.P. van de Kruijs, J. Meuldijk, J.A.J.M. Vekemans, and L.A. Hulshof Org. Process Res. Dev. 11 2007 865 869
62. F.H. Beijer, H. Kooijman, A.L. Spek, R.P. Sijbesma, and E.W. Meijer Angew. Chem., Int. Ed. 37 1998 75 78
63. G.B.W.L. Ligthart, D. Guo, A.L. Spek, H. Kooijman, H. Zuilhof, and R.P. Sijbesma J. Org. Chem. 73 2008 111 117
64. L. Perreux, and A. Loupy Tetrahedron 57 2001 9199 9223
65. A.M. Rodríguez, P. Prieto, A. de la Hoz, and A. Díaz-Ortiz Org. Biomol. Chem. 9 2011 2371 2377
66. D.J. States, R.A. Haberkorn, and D.J. Ruben J. Magn. Reson. 48 1982 286 292