Phenylboronic acid catalysed synthesis of 1,5-benzodiazepines via cyclocondensation of o-phenylenediamine and ketones

Journal of Chemical Sciences

Volumn 125, Issue 4, 2013, Pages 745-749

  Goswami, Santosh V ^a   Thorat, Prashant B ^a   Bhusare, Sudhakar R ^a  

^a DNYANOPASAK COLLEGE   (India)

Author keywords

1,5 benzodiazepines; ketones; o phenylenediamine; Phenylboronic acid

Indexed keywords

1 , 5-BENZODIAZEPINE; 1,5-BENZODIAZEPINES; EFFICIENT CATALYSTS; MILD REACTION CONDITIONS; O-PHENYLENEDIAMINE; PHENYLBORONIC ACIDS; REFLUX CONDITIONS; YIELDS OF PRODUCTS;

KETONES; ORGANIC SOLVENTS;

ORGANIC ACIDS;

EID: 84883631553     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-013-0441-7     Document Type: Article

References (37)

1. de Baun J R, Pallos, F M and Baker D R 1977 Chem. Abstracts 86 5498
2. Schultz H 1982 Benzodiazepines (Heidelberg: Springer)
3. Smiley R K 1979 Comprehensive organic chemistry (Oxford: Pergamon)
4. Landquist J K 1984 Comprehensive heterocyclic chemistry, vol. 1 (Oxford: Pergamon)
5. Randall L O, Kappel B Garattini S and Mussini E 1973 Pharmacological activity of some benzodiazepines and their metabolites, in Benzodiazepines, (eds) (New York: Raven)
6. Haris R C and Straley J M 1968 US Patent 1, 537, 757
7. El-Sayed A M, Abdel-Ghany H and El-Saghier A M M 1999 Synth. Commun. 29 3561
8. Xu J X, Wu H T and Jin S 1999 Chin. J. Chem. 17 84
9. Zhang X Y, Xu J X and Jin S 1999 Chin. J. Chem. 17 404
10. Kim K, Volkman S K and Ellman J A 1998 J. Braz. Chem. Soc. 9 375
11. Ried W and Torinus E 1959 Chem. Ber. 92 2902
12. Sabitha G, Reddy G S, Reddy K B, Reddy N M and Yadav J S 2004 Adv. Synth. Catal. 346 921
13. Luo Y Q, Xu F, Han X Y and Shen Q 2005 Chin. J. Chem. 23 1417
14. Wu J T, Xu F, Zhou Z Q and Shen Q 2006 Synth. Commun. 36 457
15. Balakrishna M S and Kaboundin B 2001 Tetrahedron Lett. 42 1127
16. Tajbakhsh M, Heravi M M, Mohajerani B and Ahmadia A N 2006 J. Mol. Catal. A: Chem. 247 213
17. Pan X Q, Zou J P, Huang Z H and Zhang W 2008 Tetrahedron Lett. 49 5302
18. Tao F and Yi W B 2008 Lett. Org. Chem. 5 655
19. Yadav J S, Reddy B V S, Praveenkumar S, Nagaiah K, Lingaiah N and Saiprasad P S 2004 Synthesis 6 901
20. Zhou X, Zhang M Y, Gao S T, Ma J J, Wang C and Liu C 2009 Chin. Chem. Lett. 20 905
21. Yi W B and Cai C 2009 J. Fluorine Chem. 130 1054
22. Vijayasankar A V, Deepa S, Venugopal B R and Nagaraju N 2010 Chin. J. Catal. 31 1321
23. Bandgar B P, Bettigeri S V and Joshi N S 2004 Synth. Commun. 34 1447
24. Yi W and Cai C 2007 Synth. Commun. 37 3827
25. Kuo C W, Wang C C, Kavala V and Yao C F 2008 Molecules 13 2313
26. Climent M J, Corma A, Iborra S and Santos L L 2009 Chem. A Eur. J. 15 8834
27. Zheng H and Hall D G 2010 Tetrahedron Lett. 51 3561
28. Frutos R P, Tampone T, Mulder J A, Xu Y, Reeves D, Wang X-J, Zhang L, Krishnamurthy D and Senanayake C H 2011 Tetrahedron Lett. 52 2465
29. Tale R H and Adude R N 2006 Tetrahedron Lett. 47 7263
30. McCubbin J A, Hosseini H and Krokhin O V 2010 J. Org. Chem. 75 959
31. Sridhar R and Perumal P T 2005 Tetrahedron 61 2465
32. Debache A, Boumoud B, Amimour M, Belfaitah A, Rhouatia S and Carbonib B 2006 Tetrahedron Lett. 47 5697
33. Lopez-Ruiz H, Briseno-Ortega H, Rojas-Lima S, Santillan R and Farfan N 2011 Tetrahedron Lett. 52 4308
34. Tibhe G D, Bedolla-Medrano M, Cativiela C and Ordonez M 2012 Synlett 23 1931
35. Goswami S V, Thorat P B and Bhusare S R 2012 Tetrahedron Lett. 53 6771
36. Goswami S V, Thorat P B and Bhusare S R 2012 Heterocycl. Commun. 18 245
37. Adude R N, Tigote R M, Goswami S V and Bhusare S R 2012 Int. J. Ind. Chem. 3 6