Microwave assisted rapid synthesis of 4-amino-3, 4-dihydroquinolin-2-ones from azetidin-2-ones

Arkivoc

Volumn 2005, Issue 1, 2004, Pages 53-64

  Shirode, Nilesh M ^a   Kulkarni, Kiran C ^a   Gumaste, Vikas K ^a   Deshmukh, Abdul Rakeeb A S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

4 amino 3,4 dihydroquinolin 2 ones; Azetidin 2 ones; Imines; Ketenes; Microwave; Transfer hydrogenation

Indexed keywords

AZETIDINE DERIVATIVE; BETA LACTAM; GLYCERYL TRINITRATE;

ARTICLE; HYDROGENATION; MICROWAVE IRRADIATION; RING OPENING; SUBSTITUTION REACTION; SYNTHESIS;

EID: 15744384430     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (54)

1. For reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982. (c) Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417-432.
2. For reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982. (c) Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417-432.
3. For reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982. (c) Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417-432.
4. For reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982. (c) Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417-432.
5. The Chemistry of β-lactams, Page, M. I.; Ed.; Chapman and Hall, London: 1992.
6. For comprehensive general reviews, see: (a) Koppel, G. A., In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219. (b) Backes, J., in Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Bayer, O., Eds; Thieme: Stuttgart, 1991; Band E16B, p 31. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, vol.1B, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Padwa, A., Pergamon: Oxford, 1996, p 507.
7. For comprehensive general reviews, see: (a) Koppel, G. A., In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219. (b) Backes, J., in Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Bayer, O., Eds; Thieme: Stuttgart, 1991; Band E16B, p 31. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, vol.1B, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Padwa, A., Pergamon: Oxford, 1996, p 507.
8. For comprehensive general reviews, see: (a) Koppel, G. A., In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219. (b) Backes, J., in Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Bayer, O., Eds; Thieme: Stuttgart, 1991; Band E16B, p 31. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, vol.1B, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Padwa, A., Pergamon: Oxford, 1996, p 507.
9. (a) Ojima, I. In "The Chemistry of β-Lactams" Georg, G. I.; Ed. VCH: New York, 1993, p 197.
10. (b) Palomo, C.; Aizpurua, J.; Ganboa, I. In "Enantioselective Synthesis of Beta-Amino Acids" Ed. Juaristi, E., Wiley-VCH, New York, 1997, p 279 and references cited therein.
11. (c) For a review on this subject see: Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377-386.
12. (d) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226-240.
13. e) Alcaide, B.; Almendros, P. Synlett 2002, 381-393.
14. Alcaide, B.; Almendros, P. Current Medicinal Chemistry 2004, 11, 1921-1949.
15. Adlington, R. M.; Baldwin J. E.; Chen, B.; Cooper, S. L.; McCoull, W.; Pritchard, G. J.; Howe, T. J.; Becker, G. W.; Hermann, R. B.; McNulty, A. M.; Neubauer, B. L. Bioorg. Med. Chem. Lett. 1997, 7, 1689-1694.
16. Han, W. T.; Trehan, A. K.; Kim Wright, J. J.; Federeci, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123-1143.
17. Borthwick, A. D.; Weingarten, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jih, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365-370.
18. (a) Burnett, D. A.; Caplen, M. A.; Davis, H. R., Jr.; Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37, 1733-1736.
19. (b) Dugar, S.; Yumibe, N.; Clader, J. W.; Vizziano, M.; Huie, K.; van Heek, M.; Compton, D. S.; Davis, H. R., Jr. Bioorg. Med. Chem. Lett. 1996, 6, 1271-1274.
20. (c) Wu, G. G. Org. Process Res. Dev. 2000, 4, 298-300.
21. (a) Doherty, J. B.; Ashe, B. M.; Agrenbright, L. W.; Barker, P. L.; Bonney, R. J.; Chandler, G. O.; Dahlgren, M. E.; Dorn, C. P., Jr.; Finke, P. E.; Firestone, R. A.; Fletcher, D.; Hagemann, W. K.; Munford, R.; O'Grady, L.; Maycock, A. L.; Pisano, J. M.; Shah, S. K.; Thomson, K. R.; Zimmerman, M. Nature 1986, 322, 192-194.
22. (b) Cvetovich, R. J.; Chartran, M.; Hartner, F. W.; Roberge, C.; Amato, J. S.; Grabowski, E. J. J. Org. Chem. 1996, 61, 6575-6580.
23. (a) Zhou, N. E.; Guo, D.; Thomas, G.; Reddy, A. V. N.; Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R. G.; Singh, R. Bioorg. Med. Chem. Lett. 2003, 13, 139-141.
24. (b) Setti, E. L.; Davis, D.; Chung, T.; McCarter, J. Bioorg. Med. Chem. Lett. 2003, 13, 2051-2053.
25. Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51-123.
26. (a) Palomo, C.; Aizpurua, J.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186-9195.
27. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oirabide, M. Eur. J. Org. Chem. 1999, 8, 3223-3235.
28. (c) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226-240.
29. (a) Govande, V. V.; Arun, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Synth. Commun. 2000, 30, 4177-4182.
30. (b) Joshi, S. N.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron: Asymmetry 2000, 11, 1477-1485.
31. (c) Krishnaswamy, D.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2000, 41, 417-419.
32. (d) Thiagarajan, K.; Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 2000, 56, 7811-7816.
33. (e) Karupaiyan, K.; Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 2000, 56, 8555-8560.
34. (f) Bhawal, B. M.; Joshi, S. N.; Krishnaswamy, D.; Deshmukh, A. R. A. S. J. Indian Inst. Sci. 2001, 81, 265-276.
35. (g) Joshi, S. N.; Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron: Asymmetry, 2001, 12, 3073-3076.
36. (h) Arun, M.; Govande, V. V.; Deshmukh, A. R. A. S. Bhawal, B. M. Indian J. Chem. 2002, 41B, 856-857.
37. (i) Krishnaswamy, D.; Govande, V. V.; Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron 2002, 58, 2215-2225.
38. (j) Patil, R. T.; Parveen, G.; Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Synlett 2002, 1455-1458.
39. (k) Joshi, S. N.; Phalgune, U. D.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2003, 44, 1827-1830.
40. (l) Arun, M.; Joshi, S. N.; Puranik, V. G.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron 2003, 59, 2309-2316.
41. (m) Shinkre, B. A.; Puranik, V. G.; Bhawal, B. M.; Deshmukh A. R. A. S. Tetrahedron: Asymmetry 2003, 14, 453-459.
42. (n) Jayanthi, A.; Gumaste, V. K.; Deshmukh, A. R. A. S. Synlett 2004, 979-982.
43. (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 8989-9004.
44. (b) Jayaraman, M.; Puranik, V. G.; Bhawal, B. M. Tetrahedron 1996, 52, 9005-9016.
45. (c) Srirajan, V.; Deshmukh, A. R. A. S.; Puranik, V. G.; Bhawal, B. M. Tetrahedron: Asymmetry 1996, 7, 2733-2738.
46. (d) Krishnaswamy, D.; Govande, V. V.; Deshmukh, A. R. A. S. Synthesis 2003, 12, 1903-1908.
47. (e) Deshmukh, A. R. A. S.; Bhawal, B. M.; Krishnaswamy, D.; Govande, V. V.; Shinkre, B. A.; Jayanthi, A. Current Medicinal Chemistry 2004, 11, 1889-1920.
48. Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349-3352.
49. (a) Hayes, B. L. Microwave Synthesis: Chemistry at Speed of Light, CEM Publishing, Mathews, NC, USA, 2002.
50. (b) Varma, R. S. Microwaves in Organic Syntheses, Ed. A. Loupy, Wiley-VCH, New York, 2002, pp181-218.
51. (c) Varma, R. S. Advances in Green Chemistry: Chemical Syntheses using Microwave Irradiation, Astra Zeneca, Research Foundation, Banglore, India, 2003.
52. (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Tetrahedron 1999, 55, 10851-10870.
53. (e) Bose, A. K.; Banik, B. K.; Lavlinskaia, N.; Jayaraman, M.; Manhas, M. S. Chemtech 1997, 18-24.
54. (f) Caddick, S. Tetrahedron 1995, 51, 10403-10432.