Heteroaromatic annulation studies on 10,11-dihydro-11-[bis(methylthio)methylene]dibenzoxepin-10-one: a facile access to novel dibenzoxepino[4,5]-fused heterocycles

Tetrahedron

Volumn 63, Issue 40, 2007, Pages 10067-10076

  Kumar, Sarvesh ^a   Ila, Hiriyakkanavar ^a   Junjappa, Hiriyakkanavar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Oxoketene dithioacetal; Dibenzoxepine; Heteroaromatic annulation; Heterocycles

Indexed keywords

10,11 DIHYDRO 11 [BIS(METHYLTHIO)METHYLENE]DIBENZOXEPIN 10 ONE; ANTIDEPRESSANT AGENT; ANXIOLYTIC AGENT; ASENAPINE; BELOXEPIN; DIBENZOXEPIN DERIVATIVE; GAMMA LACTONE DERIVATIVE; GUANIDINE; HETEROCYCLIC COMPOUND; HYDRAZINE; HYDROXYLAMINE; ISOXAZOLE DERIVATIVE; NITRILE; ORG 4428; PIPERIDINE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; THIOPHENE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSYCHOPHARMACOLOGY; SYNTHESIS;

EID: 34547943871     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.045     Document Type: Article

References (65)

1. Olivera R., SanMartin R., Churruca F., and Dominguez E. J. Org. Chem. 67 (2002) 7215 and references therein
2. SanMartin R., Olivera R., Churrucka F., Tellitu I., and Dominguez E. Trends Heterocycl. Chem. 9 (2003) 259
3. Mercep, M.; Mesic, M.; Pesic, D. WO 2003099822, 2003;
4. Peggy Paduraru M., and Wilson P.D. Org. Lett. 5 (2003) 4911
5. Review:. Missir A., Limban C., Stecoza C., Morusciag L., and Chirita I. Farmacia (Bucharest) 46 (1998) 17
6. Bischoff S. Novel Antipsychotic Drugs (1992), Meltzer, New York, NY pp 117-134
7. Storni A. Actual Chim. Ther. 16 (1989) 143
8. Review:. Zimmermann K., Waldmeier P.C., and Tatton W.G. Pure Appl. Chem. 71 (1999) 2039
9. Prinssen E.P., Koek W., and Kleven M.S. Eur. J. Pharmacol. 388 (2000) 57
10. Miguel-Hidalgo J.J. Drugs 2 (2000) 85
11. Andree B., Halidin C., Vrijmoed-De Vries M., and Farde L. Psychopharmacology 131 (1997) 339
12. Martin, L. L.; Setescak, L. L. U.S. Patent 4,576,960, 1986;
13. Chem. Abstr. 104 (1986) 224840
14. Cherkofsky, S. C.; Sharpe, T. R. U.S. Patent 4,198,421, 1980;
15. Chem. Abstr. 93 (1980) 71783
16. Kumazawa, T.; Ohsima, E.; Obase, H. JP 61152673, 1987;
17. Chem. Abstr. 106 (1987) 4904
18. Bracaccio G., Lettiere G., Monforte P., and Larizza A. Farmaco 37 (1982) 711
19. Zimmermann, K.; Roggo, S.; Betschart, C. WO 9745422, 1997;
20. Chem. Abstr. 128 (1998) 61439
21. Jinno S., and Okita T. Heterocycles 51 (1999) 303
22. Yamashita, S.; Takeo, J.; Jinno, S.; Kogure, Y.; Onuki, H.; Okita, T.; Hata, J.; Fukuda, Y.; Ohtsuka, N. WO 9725985, 1997;
23. Chem. Abstr. 127 (1997) 149089
24. Jinno, S.; Okita, T.; Ohtsuka, N.; Yamashita, S.; Hata, J.; Takeo, J. WO 0075127, 2000;
25. Chem. Abstr. 134 (2001) 29329
26. Nakazawa, H.; Ando, K.; Kuge, Y.; Sugaya, T.; Kasai, M.; Tomioka, S. JP 06306070;
27. Chem. Abstr. 122 (1995) 160492
28. Kanamaru, T.; Hida, T.; Muroi, M. EP 342665, 1989;
29. Chem. Abstr. 113 (1990) 5954
30. Reviews:
31. Ila H., Junjappa H., and Mohanta P.K. In: Gribble G.W., and Gilchrist T.L. (Eds). Progress in Heterocyclic Chemistry Vol. 13 (2001), Pergamon, Oxford 1-24 Chapter 1
32. Junjappa H., Ila H., and Asokan C.V. Tetrahedron 46 (1990) 5423
33. Recent papers on heteroaromatic annulation:
34. Panda K., Venkatesh C., Ila H., and Junjappa H. Eur. J. Org. Chem. (2005) 2045
35. Peruncheralathan S., Khan T.A., Ila H., and Junjappa H. Tetrahedron 60 (2004) 3457
36. Panda K., Siddiqui I., Mahata P.K., Ila H., and Junjappa H. Synlett (2004) 449
37. Mahata P.K., Venkatesh C., Syam Kumar U.K., Ila H., and Junjappa H. J. Org. Chem. 68 (2003) 3966
38. Panda K., Suresh J.R., Ila H., and Junjappa H. J. Org. Chem. 68 (2003) 3498
39. Mahata P.K., Syam Kumar U.K., Sriram V., Ila H., and Junjappa H. Tetrahedron 59 (2003) 2631
40. Suresh J.R., Syam Kumar U.K., Ila H., and Junjappa H. Tetrahedron 57 (2001) 781
41. Basaveswara Rao M.V., Syam Kumar U.K., Ila H., and Junjappa H. Tetrahedron 55 (1999) 11563
42. Ueda I., Sato Y., Maeno S., and Umio S. Chem. Pharm. Bull. 23 (1975) 2223
43. Chauhan S.M.S., and Junjappa H. Synthesis (1974) 880
44. Chauhan S.M.S., and Junjappa H. Tetrahedron 32 (1976) 1779
45. Singh G., Bhattacharjee S.S., Ila H., and Junjappa H. Synthesis (1982) 693
46. Chauhan S.M.S., and Junjappa H. Synthesis (1975) 798
47. Peruncheralathan S., Khan T.A., Ila H., and Junjappa H. J. Org. Chem. 70 (2005) 10030
48. Peruncheralathan S., Yadav A.K., Ila H., and Junjappa H. J. Org. Chem. 60 (2005) 9644
49. Purkayastha M.L., Ila H., and Junjappa H. Synthesis (1989) 20
50. Bhat L.N., Thomas A., Ila H., and Junjappa H. Tetrahedron 48 (1992) 10377
51. Thomas A., Singh G., Ila H., and Junjappa H. Tetrahedron Lett. 30 (1989) 3093
52. Okazaki R., Negishi Y., and Inamoto N. J. Chem. Soc., Chem. Commun. (1982) 1055
53. Okazaki R., Negishi Y., and Inamoto N. J. Org. Chem. 49 (1984) 3819
54. Rastogi R.R., Kumar A., Ila H., and Junjappa H. J. Chem. Soc., Perkin Trans. 1 (1978) 549
55. Rastogi R.R., Ila H., and Junjappa H. J. Chem. Soc., Chem. Commun. (1975) 645
56. Gupta A.K., Ila H., and Junjappa H. Tetrahedron 46 (1990) 3703
57. Barun O., Patra P.K., Ila H., and Junjappa H. Tetrahedron Lett. 40 (1999) 3797
58. Potts K.T., Cipullo M.J., Ralli P., and Theodoridis G. J. Am. Chem. Soc. 103 (1981) 3585
59. Reviews:
60. Ila H., Junjappa H., and Barun O. J. Organomet. Chem. 624 (2001) 34
61. Junjappa H., and Ila H. Phosphorous, Sulfur Silicon Relat. Elem. 95 (1994) 35
62. Singh G., Ila H., and Junjappa H. Tetrahedron Lett. 25 (1984) 5095
63. Neale A.J., Rawlings T.J., and McCall E.B. Tetrahedron 21 (1965) 1299
64. Balu M.P., Singh G., Ila H., and Junjappa H. Tetrahedron Lett. 27 (1986) 117
65. Rao C.S., Balu M.P., Ila H., and Junjappa H. Tetrahedron 47 (1991) 3499