Facile one pot synthesis of dioxazadibenzocyclodecene-6-one, 6-thione and other homologues

Arkivoc

Volumn 2009, Issue 7, 2009, Pages 189-196

  Singh, M S ^a   Singh, Pratibha ^a   Singh, Pallavi ^a   Gupta, Ashutosh ^b  

^a BANARAS HINDU UNIVERSITY   (India)

^b UDAI PRATAP AUTONOMOUS COLLEGE   (India)

Author keywords

Dioxazadibenzocyclodecene 6 one; N (2 hydroxymethylphenyl) salicylideneimine; O aminobenzyl alcohol; Salicylaldehyde

Indexed keywords

EID: 71049138435     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0010.718     Document Type: Article

References (50)

1. Roth, H. J.; Kleemann, A. Pharmaceutical Chemistry; Vol. 1: Drug Synthesis. Wiley: New York, 1988.
2. Katritzky, A. R.; Rees, C. W., Eds.; Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Vol. 1, Chapter 1:06.
3. Katritzky, A. R.; Rees, C. W., Eds.; Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5:18.
4. Mohiuddin, G.; Reddy, P. S.; Ahmed, K.; Ratnam, C. V. Heterocycles 1986, 24, 3489.
5. Frostl, W.; Maitre, L. Pharmacopsychiatry 1989, 22, 54.
6. Walser, A.; Fryer, R. I. Bicyclic Diazepines; Wiley: New York, 1991; Chapter VII.
7. (a) For the procedure used in this study, see: Campbell, K. N.; Sommers, A. H.; Campbell, B. K. J. Am. Chem. Soc. 1944, 66, 82;
8. In general: (b) Patai, S. The Chemistry of the Carbon-Nitrogen Double Bond; Interscience: New York, 1970.
9. For representative examples, see: (a) Boger, D. L. Tetrahedron 1983, 39, 2869;
10. (b) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087;
11. (c) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753;
12. (d) Sainte, F.; Serckx-Poncin, B.; Hesbain-Frisque, A. M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428;
13. (e) Cheng, Y. S.; Lupo, A. T.; Fowler, F. W. J. Am. Chem. Soc. 1983, 105, 7696;
14. (f) Cheng, Y. S.; Fowler, F. W.; Lupo, A. T. J. Am. Chem. Soc. 1981, 103, 2090;
15. (g) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: New York, 1987;
16. (h) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16 and references therein.
17. (a) Ha, D. C.; Hart, D. J.; Yang, T. K. J. Am. Chem. Soc. 1984, 106, 4819;
18. (b) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Org. Chem. 1985, 50, 3115;
19. (c) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1984, 106, 5031;
20. (d) Nagao, Y.; Dai, W. M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Am. Chem. Soc. 1988, 110, 289;
21. (e) Volkmann, R. A.; Davis, J. T.; Meltz, C. N. J. Am. Chem. Soc. 1983, 105, 5946;
22. (f) Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503.
23. Yadav, J. S.; Reddy, B. V. S.; Kumar, P. S.; Nagaiah, K.; Lingaiah, N.; Saiprasad, P. S. Synthesis 2004, 901.
24. Jorgensen, M. R.; Mc Cleland, C. W. Taljaard, B. J. Chem. Res. (S) 1997, 356.
25. Evans, P. A.; Holmes. B. Tetrahedron 1991, 47, 9131.
26. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
27. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223.
28. Green, D. L. C.; Thompson, C. M. Tetrahedron 1991, 32, 5051.
29. (a) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, Florida, 1994.
30. (b) Langer, P.; Freiberg, W. Chem. Rev. 2004, 104, 4125.
31. (a) Singh, M. S.; Singh, A. K. Synth. Commun. 2000, 30, 53.
32. (b) Singh, M. S.; Singh, A. K. Heterocycles 2000, 53, 851.
33. (a) Singh, M. S.; Singh, A. K. Indian J. Chem. 2000, 39B, 551;
34. (b) Singh, M. S.; Pandey, G. Synth. Commun. 2000, 30, 3589;
35. (c) Singh, M. S.; Singh, B, K.; Singh, A. K. Indian J. Chem. 2002, 41B, 1507.
36. (a) Singh, M. S.; Singh, A. K. Synthesis 2004, 837.
37. (b) Singh, M. S.; Singh, P. Synth. Commun. 2008, 38, 775.
38. (c) Singh, M. S.; Singh, A. K. Tetrahedron Lett. 2005, 46, 315.
39. (a) Tarafder, M. T. H.; Khan, A. R. Polyhedron 1991, 10, 819.
40. (b) Atwood, D. A.; Harvey, M. J. Chem. Rev. 2001, 101, 37.
41. (c) Syamal, A.; Kale, K. S. Indian J. Chem. 1980, 19A, 486.
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785.
44. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta.1973, 28, 213.
45. GAUSSIAN 03, Gaussian, Inc., Wallingford CT, USA, 2004.
46. Potts, K. T.; Husain S. J. Org. Chem. 1971, 36, 10.
47. th Edn., 1998.
48. (a) Nakanishi, K. Infrared Spectra of Inorganic and Coordination Compounds; Wiley: New York, 1970;
49. (b) Bellamy, L. J. Advances in Infrared Group Frequencies; Chapman and Hall: London, 1968.
50. th Edn., Butterworth: Heinemann, Oxford, OX2 8DP, 1997.