Regioselective aminoethylation of 1,4-benzodiazepin-2-one under conventional heating and microwave irradiation

Tetrahedron Letters

Volumn 47, Issue 20, 2006, Pages 3357-3360

  Mishra, Jitendra Kumar ^a   Srinivasa Rao, J ^b   Narahari Sastry, G ^b   Panda, Gautam ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPIN 2 ONE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEAT TREATMENT; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33646020376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.094     Document Type: Article

References (25)

1. Gedye R.N., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., and Rousell J. Tetrahedron Lett. 27 (1986) 279
2. Majetich G., and Wheless K. Microwave-Enhanced Chemistry. Fundamentals. In: Kingston H.M., and Haswell S.J. (Eds). Sample Preparations and Applications (1997), American Chemical Society, Washington, DC Chapter 8
3. Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199
4. Galema S. Chem. Soc. Rev. 26 (1997) 233
5. Bose A.K., Manhas M.S., Ganguly S.N., Sharma A.H., and Banik B.K. Synthesis (2002) 1578
6. Loupy A., Petit A., Hamelin J., Texier-Boullet F., Jacquault P., and Mathe D. Synthesis (1998) 1213
7. Galema S. Chem. Soc. Rev. 26 (1997) 233
8. Verma R.S. Green Chem. 1 (1999) 43
9. Bose A.K., Banik B.K., and Manhas M.S. Tetrahedron Lett. 36 (1995) 213
10. Stuerga D., Gonon K., and Lallemant M. Tetrahedron 49 (1993) 6229
11. Manhas M.S., Banik B.K., Mathur A., Vincent J.E., and Bose A.K. Tetrahedron 56 (2000) 5587
12. Almena I., Diaz-Ortiz A., Diaz-Barra E., De la Hoz A., and Loupy A. Chem. Lett. 37 (1996) 333
13. ForFar I., Cabildo P., Claramunt R.M., and Elguero J. Chem. Lett. (1994) 2079
14. Langa F., de la Cruz P., de la Hoz A., Espildora E., Cossio F.P., and Lecea B.J. Org. Chem. 65 (2000) 2499
15. Vega J.A., Cueto S., Ramos A., Vaquero J.J., Garcia-Navio J.L., Alvarez-Builla J., and Ezquerra J. Tetrahedron Lett. 37 (1996) 6413
16. Hosseinzadeh R., Tajbakhsh M., Lasemi Z., and Sharifi A. Bull. Korean Chem. Soc. 25 (2004) 1143
17. Loupy A., Perreux L., Liagre M., Burle K., and Moneuse M. Pure Appl. Chem. 73 (2001) 161
18. Mishra J.K., and Panda G. Synthesis (2005) 1881
19. 3 (942 mg, 6.82 mmol), and dry DMF (10 ml) was heated for 6-8 h at 80 °C. Work-up and column chromatography over silica gel furnished 2a-d.
20. Aminoethylation of 1,4-benzodiazepin-2-one under microwave conditions: Domestic microwave oven-power input: 230 V AC/50 Hz; Output: 900 W (IEC 705 rating standard); microwave frequency: 2450 MHz; power consumption, microwave 1350 W. As described above instead of heating for 6-8 h at 80 °C, the mixture was irradiated with microwaves for 90 s.
21. Langa F., De La Cruz P., De La Hoz A., Diaz-Ortiz A., and Diez-Barra E. Contemp. Org. Synth. 4 (1997) 373
22. Hammond G.S. J. Am. Chem. Soc. 77 (1955) 334
23. Lewis D.A. Mater. Res. Soc. Symp. Proc. 269 (1992) 21
24. Mingos D.M.P. Chem. Ind. (London) (1994) 596
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D.J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision A.1; Gaussian, Inc., Pittsburgh, PA, 2003.