[(L)proline]2Zn catalysed synthesis of 1,5-benzodiazepine derivatives under solvent-free condition

Synthetic Communications

Volumn 34, Issue 21, 2004, Pages 3833-3846

  Sivamurugan, V ^a   Deepa, K ^a   Palanichamy, M ^a   Murugesan, V ^a  

^a ANNA UNIVERSITY   (India)

Author keywords

1,5 Benzodiazepine; Lewis acid; Multi component reaction; One pot condensation; Solvent free; Zn proline

Indexed keywords

2 BUTANONE; 2 ETHYL 2,3,4 TRIMETHYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2 METHYL 2,4 DI(4 BROMOPHENYL) 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2 METHYL 2,4 DI(4 CHLOROPHENYL) 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2 METHYL 2,4 DI(4 HYDROXYPHENYL) 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2 METHYL 2,4 DIPHENYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2 PENTANONE; 2,2,4 TRIETHYL 3 METHYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 2,2,4 TRIMETHYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 3 ETHYL 2,2,4 TRI N PROPYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 3 ETHYL 2,4 DIMETHYL 2 N PROPYL 2,3 DIHYDRO 1H 1,5 BENZODIAZEPINE; 3 PENTANONE; 4 CHLOROACETOPHENONE; 4 HEPTANONE; ACETONE; ACETOPHENONE; ACETOPHENONE DERIVATIVE; ALKANONE; BENZODIAZEPINE DERIVATIVE; CYCLOHEPTANONE; CYCLOHEXANONE; DIAZEPINE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; PROLINE DERIVATIVE; SOLVENT; SPIROCYCLOHEPTAN 6,7,8,9,10,10A,11,12 OCTAHYDROBENZO[B]CYCLOHEPTA[E][1,4]DIAZEPINE; SPIROCYCLOHEXAN 2,3,4,10,11,11A HEXAHYDRO 1H DIBENZO[B,E][1,4]DIAZEPINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; INFRARED SPECTROSCOPY; MICROWAVE RADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; RECYCLING; REPRODUCIBILITY; STRUCTURE ANALYSIS; TECHNIQUE; ULTRAVIOLET SPECTROSCOPY;

EID: 7644243788     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200034752     Document Type: Article

References (20)

1. De Baun, J.R.; Pallos, F.M.; Baker, D.R. 5-Furoyl-2,2,4-trimethyl-2,5- dihydro-1H-1,5-benzodiazepine as an anti-inflammatory agent. US Patent 3, 978, 227, 1976; Chem. Abstr. 1977, 86, 5498d.
2. (a) Schultz, H. Benzodiazepines; Springer: Heidelberg, 1982;
3. (b) Smailey, R.K. Comprehensive Organic Chemistry; Barton, D., Ollis, W.D., Eds.; Pergamon: Oxford, 1979; Vol. 4, 600;
4. (c) Landquist, J.K. Comprehensive Heterocyclic Chemistry; Katritzky, A.R., Rees, C.W., Eds.; Pergamon: Oxford, 1984; Vol. 1, 166, 170.
5. Randall, L.O.; Kappel, B. Benzodiazepines; Garattini, S., Mussini, E., Randall, L.O., Eds.; Raven Press: New York, 1973; 27.
6. Stahlofen, P.; Ried, W. Heterocyclic seven-membered ring systems. V. Reaction of o-phenylene diamine with α/β-unsaturated carbonyl compounds. Chem. Ber. 1957, 90, 815-824.
7. Ried, W.; Torinus, E. Heterocyclic seven-membered ring systems. X. Synthesis of condensed 5-, 7-, & 8-membered heterocycles with 2-nitrogen atoms. Chem. Ber. 1959, 92, 2902-2916.
8. Herbert, J.A.L.; Suschitzky, H.J. Syntheses of heterocycles compounds. Part XXIX. Substituted 2,3-dihydro-1H-1,5-benzodiazepines. J. Chem. Soc., Perkin Trans. 1 1974, 2657-2661.
9. Morales, H.R.; Bulbarela, A.; Contreras, R. New synthesis of dihydro and heterohydro-1,5-benzodiazepines by reductive condensation of o-phenylene diamine and ketones in the presence of sodium borohydride. Heterocycles 1986, 24, 135-139.
10. 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.
11. Balakrishna, M.S.; Kaboudin, B. A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface. Tetrahedran Lett. 2001, 42, 1127-1129.
12. Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives. Tetrahedran Lett. 2001, 42, 3193-3195.
13. Jarikote, D.V.; Siddiqui, S.A.; Rajagopal, R.; Thomas, D.; Lahoti, R.J.; Srinivasan, K.V. Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions. Tetrahedran Lett. 2003, 44, 1835-1838.
14. Reddy, B.M.; Sreekanth, P.M. An efficient synthesis of 1,5-benzodiazepine derivatives catalysed by a solid superacid sulfated zirconia. Tetrahedran Lett. 2003, 44, 4447-4449.
15. (a) Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074;
16. (b) Gareth, W.W.C.; Colin, L.R.; Janet, L.S. Recent advances in solvent less organic reactions towards benign synthesis with remarkable versatility. Chem. Commun. 2001, 2159-2169.
17. (a) Varma, R.S. Solvent-free organic syntheses using supported reagents and microwave irradiation. Green Chemistry 1999, 43-55;
18. (b) Lidstrom, P.; Tierny, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - a review. Tetrahedran 2001, 57, 9225-9283.
19. Kaboudin, B.; Navace, B. Alumina/phosphorous pentaoxide (APP) as an efficient reagent for the synthesis of 1,5-benzodiazepines under microwave irradiation. Heterocycles 2001, 55, 1443-1446.
20. Minothora, P.; Julia, S.S.; Constatinos, A.T. An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent. Tetrahedran Lett. 2002, 43, 1755-1758.