Preyssler catalyst-promoted rapid, clean, and efficient condensation reactions for 3H-1,5-benzodiazepine synthesis in solvent-free conditions

Tetrahedron Letters

Volumn 54, Issue 48, 2013, Pages 6574-6579

  Pasquale, Gustavo A ^a,b   Ruiz, Diego M ^a   Jios, Jorge L ^c   Autino, Juan C ^a   Romanelli, Gustavo P ^a,b  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

^b FACULTAD DE CIENCIAS AGRARIAS Y FORESTALES   (Argentina)

^c UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

Author keywords

1,3 Diaryl 1,3 propanediones; 3H 1,5 Benzodiazepines; o Phenylenediamine; Preyssler catalyst; Solvent free

Indexed keywords

1 (2 HYDROXYPHENYL) 3 PHENYL 1,3 PROPANEDIONE; 2 PHENYLENEDIAMINE DERIVATIVE; 3H 1,5 BENZODIAZEPINE; BENZODIAZEPINE DERIVATIVE; DIAMINE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; INFRARED SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84886786739     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.09.101     Document Type: Article

References (44)

1. H. Schultz Benzodiazepines 1982 Springer, Heidelberg Germany
2. L.O. Randall, and B. Kappel S. Garattini, E. Mussini, L.O. Randall, Benzodiazepines 1973 Raven Press New York
3. J.K. Landquist A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry 1984 Pergamon Oxford, UK
4. X. Pan, Z. Zou, and W. Zhang Tetrahedron Lett. 49 2008 5302 5308
5. C. Radatz, R. Silva, G. Perin, E. Lenardao, R. Jacob, and D. Alves Tetrahedron Lett. 52 2011 4132 4136
6. M. Abdollahi-Alibeik, I. Mohammadpoor-Baltork, Z. Zaghaghi, and B. Yousefi Catal. Commun. 9 2008 2496 2502
7. K.S. Atwal, J.L. Bergey, A. Hedberg, and S. Moreland J. Med. Chem. 30 1987 635 640
8. M.D. Braccio, G. Grossi, G. Roma, L. Vargiu, M. Mura, and M.E. Marongiu Eur. J. Med. Chem. 36 2001 935 949
9. R.J. Reddy, D. Ashok, and P.N. Sharma Indian J. Chem. B32 1993 404 410
10. D.P. Clifford, D. Jackson, R.V. Edwards, and P. Jeffrey Pestic. Sci. 7 1976 453 458
11. S. Majid, W. Khanday, and R. Tomar J. Biomed. Biotechnol. 2012 6
12. D. Jung, J. Song, Y. Kin, D. Lee, Y. Lee, Y. Park, S. Choi, and J. Hahn Bull. Korean Chem. Soc. 28 2007 1877 1880
13. J.A.L. Herbert, and H. Suschitzky J. Chem. Soc., Perkin Trans. 1 1974 2657 2661
14. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Tetrahedron Lett. 42 2001 3193 3195
15. X.Q. Pan, J.P. Zou, Z.H. Huang, and W. Zhang Tetrahedron Lett. 49 2008 5302 5308
16. H.R. Morales, A. Bulbarela, and R. Contreras Heterocycles 24 1986 135 139
17. M.S. Balakrishna, and B. Kaboudin Tetrahedron Lett. 42 2001 1127 1129
18. R. Kumar, P. Chaudhary, S. Nimesh, A.K. Verma, and R. Chandra Green Chem. 8 2006 519 521
19. W.Y. Chen, and J. Lu Synlett 2005 1337 1339
20. P. Minothora, S.S. Julia, and A.T. Constantinos Tetrahedron Lett. 43 2002 1755 1758
21. D.V. Jarikote, S.A. Siddiqui, R. Rajagopal, D. Thomas, R.J. Lahoti, and K.V. Srinivasan Tetrahedron Lett. 44 2003 1835 1838
22. B.M. Reddy, P.M. Sreekamth, and V.R. Reddy J. Mol. Catal. A 225 2005 71 78
23. B. Kaboudin, and K. Navaee Heterocycles 55 2001 1443 1446
24. M.A. Chari, and K. Syamasundar Catal. Commun. 6 2005 67 70
25. A. Hegedüs, Z. Hell, and A. Potor Catal. Lett. 105 2005 229 232
26. M. Muñoz, G. Sathicq, G. Romanelli, S. Hernández, C. Cabello, I. Botto, and M. Capron J. Porous Mater. 20 2013 65 73
27. M. Heravi, S. Sadjadi, H. Oskooie, R. Hekmatshoar, and F. Bamoharram J. Chin. Chem. Soc. 55 2008 842 845
28. J.S. Yadav, B.V.S. Reddy, S. Praveenkumar, K. Nagaiah, N. Lingaiah, and P.S. Saiprasad Synthesis 2004 901 904
29. W. Watson Green Chem. 14 2012 251 256
30. S. Kalidindi, and B. Jagirdar ChemSusChem 5 2012 65 75
31. M. Mulvihill, M. Beach, E. Zimmerman, and P. Anastas Annu. Rev. Environ. Resour. 36 2011 271 293
32. M. Singh, and S. Chowdhury RSC Advances 2 2012 4547 4592
33. W. Shearouse, D. Waddell, and J. Mack Curr. Opin. Drug Disc. Dev. 12 2009 772 783
34. P. Kalita, and R. Kumar Microporous Mesoporous Mater. 149 2012 1 9
35. G. Nagendrappa Resonance 2002 59 68
36. M.N. Timofeeva Appl. Catal. A: General 256 2003 19 35
37. G. Romanelli, and J. Autino Mini-Rev. Org. Chem. 6 2009 359 366
38. G. Romanelli, E. Virla, P. Duchowicz, A. Gaddi, D. Ruiz, D. Bennardi, E. Del Velle Ortíz, and J. Autino J. Agric. Food Chem. 58 2010 6290 6295
39. G. Romanelli, D. Ruiz, J. Autino, and H. Giaccio Mol. Diversity 14 2010 803 807
40. R. Ruiz, G. Romanelli, P. Vázquez, and J. Autino Appl Appl. Catal. A: General 374 2010 110 119
41. G. Romanelli, D. Ruiz, P. Vázquez, H. Thomas, and J. Autino Chem. Eng. J. 161 2010 355 362
42. C. Tsoleridis, M. Pozarentzi, S. Mitkidou, and J. Stephanatou ARKIVOC XV 2008 193 209
43. M. Takahashi, T. Takada, and T. Sakagami J. Heterocycl. Chem. 24 1987 797 799
44. R. Ahmad, M. Zia-Ul-Haq, S. Hameed, H. Nadeem, and H. Duddeck J. Chem. Soc. Pak. 22 2000 302 308