Perchloric acid supported on silica catalyzed efficient synthesis of 1,5-benzodiazepines

Synthetic Communications

Volumn 37, Issue 23, 2007, Pages 4117-4122

  Meshram, H M ^a   Reddy, P N ^a   Murthy, P Vishnu ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

HClO4 SiO2; Ketones; O phenylenediamines

Indexed keywords

2,2,4 TRIMETHYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPIN 8 YLCHLORIDE; BENZODIAZEPINE DERIVATIVE; KETONE DERIVATIVE; PERCHLORIC ACID; SILICA GEL; SOLVENT; SPIRO[CYCLOHEXANE 1,11' (2',3',4',10',11',11A' HEXAHYDRO 10H DIBENZO[B,E][1,4]DIAZEPINE)]; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; CATALYSIS; CATALYST; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DRUG SYNTHESIS;

EID: 37049036857     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701572936     Document Type: Article

References (22)

1. (a) Schutz, H. Benzodiazepines; Springer: Heidelberg, 1982;
2. (b) Landquist, J. K. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R. and Rees, C. W. Eds.; Pergamon: Oxford, 1984, Vol. 1, p. 166.
3. Randall, L. O.; Kappel, B. Benzodiazepines; Garattini, S., Mussini, E., and Randall, L. O. Eds.; Raveen Press: New York, 1973, p. 27.
4. (a) Essaber, M.; Baouid, A.; Hasnaoui, A.; Benharref, A.; Lavergne, J. P. Synthesis of new tri- and tetra heterocyclic systems: 1,3-Dipolar cycloadition of nitrilmines on 2,7-dimethyl-4-phenyl-3H-1,5-benzodiazepine. Synth. Commun. 1998, 28, 4097-4104;
5. (b) El-Sayed, A. M.; Abdel-Ghany, H.; El-Saghier, A. M. M. A novel synthesis of pyrano (2,3-C)-,1,3-oxazino (2,3b)-,1,2,4-triazolo(3,4-b)-, oxazolo (2,3-b)-, furano (3,2-c)-, and 3-substituted-(1,5) benzodiazepin-2-ones. Synth. Commun. 1999, 29, 3561-3572;
6. (c) Reddy, K. V. V.; Rao, P. S.; Ashok, D. A facile synthesis of 2-benzoyl-6-hydroxy-3-methyl-5-(2-substited-2,3-dihydro-1H-1, 5-benzodiazepin-4-yl) benzo(b) furans. Synth. Commun. 2000, 30, 1825-1836.
7. Herbert, J. A. L.; Suschitzky, H. Synthesis of heterocyclic compounds, part XXIX: Substituted 2,3-dihydro-1h-1,5-benzodiazepines. Chem. Soc., Perkin Trans. 1 1974, 1, 2657-2661.
8. Jung, D. I.; Choi, T. W.; Kim, Y. Y.; Kim, I. S.; Park, Y. M.; Lee, Y. G.; Jung, D. H. Synthesis of 1,5-benzodiazepine derivatives. Synth. Commun. 1999, 29, 1941-1951.
9. Morales, H. R.; Bulbarela, A.; Contreras, R. New synthesis of dihydro- and tetrahydro-1,5-benzodiazepines by reductive condensation of O-phenylenediamine and ketones in the presense of sodiumborohydride. Heterocycles 1986, 24, 135-139.
10. Balakrishna, M. S.; Kabouding, B. Simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface. Tetrahedron Lett. 2001, 42, 1127-1129.
11. (a) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett. 2001, 42, 3193-3195;
12. (b) De, S. K.; Gibbs, R. A. Scandium (lll) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett. 2005, 46, 1811-1813.
13. Yadav, J. S.; Reddy, B. V. S.; PraveenKumar, S.; Nagaiah, K. Indium(lll) bromide: a novel and efficient reagent for the rapid synthesis of 1,5-benzodiazepine derivatives. Synthesis 2005, 480-484.
14. (a) Jarikote, D. V.; Siddiqui, S. A.; Rajagopal, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Room-temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions. Tetrahedron Lett. 2003, 44, 1835-1838;
15. (b) Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Anuradha, K. Amberlyst-15: a novel and recyclable reagent for the synthesis of 1,5-benzodiazepines in ionic liquids. Green Chem. 2002, 4, 592-594.
16. Minothora, P.; Julia, S. S.; Constantinos, A. An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent. Tetrahedron Lett. 2002, 43, 1755-1758.
17. (a) Samajdar, S.; Becker, F. R.; Naik, P. K. Surface-mediated highly efficient regio-selective nitration of aromatic compounds by bismuth nitrate. Tetrahedron Lett. 2000, 41, 8017-8020;
18. 3 (40%) - A mild, efficient, and reusable catalyst/reagent system for the selective mono nitration and benzylic oxidations. Synth. Commun. 2002, 32, 3565-3574;
19. (c) Srinivas, K. V. N. S.; Das, B. An efficient one-pot synthesis of pyrano- and furoquinolines employing two reusable solid acids as heterogeneous catalysta. Synlett. 2004, 1715-1718.
20. (a) Chakraborti, A. K.; Gulhane, R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alconols, and amines. Chem. Commun. 2003, 1896-1897;
21. 4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glucals. J. Org. Chem. 2004, 69, 6137-6140;
22. 2 catalyzed per-O-acetylation of carbohydrates. Carbohydrate Res. 2005, 325-329.