Aryl-fused nitrogen heterocycles by a tandem reduction-Michael addition reaction

Journal of Organic Chemistry

Volumn 65, Issue 9, 2000, Pages 2847-2850

  Bunce, Richard A ^a   Herron, Derrick M ^a   Ackerman, Matthew L ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; NITROGEN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DERIVATIZATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; NITROGEN; OXIDATION-REDUCTION; SPECTRUM ANALYSIS;

EID: 0034607870     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991899+     Document Type: Article

References (54)

1. Oklahoma State University Freshman Research Scholar, 1999-2000.
2. For recent reviews on tetrahydroquinolines, see: (a) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785. (b) Katritsky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070. See also: (c) Gilchrist, T. L.; Rahman, A. J. Chem. Soc., Perkin Trans. 1 1998, 1203-1207. (d) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Nishimura, H.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M.; Ogita, K.; Yoneda, Y. J. Med. Chem. 1994, 37, 3956-3968.
3. For recent reviews on tetrahydroquinolines, see: (a) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785. (b) Katritsky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070. See also: (c) Gilchrist, T. L.; Rahman, A. J. Chem. Soc., Perkin Trans. 1 1998, 1203-1207. (d) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Nishimura, H.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M.; Ogita, K.; Yoneda, Y. J. Med. Chem. 1994, 37, 3956-3968.
4. For recent reviews on tetrahydroquinolines, see: (a) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785. (b) Katritsky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070. See also: (c) Gilchrist, T. L.; Rahman, A. J. Chem. Soc., Perkin Trans. 1 1998, 1203-1207. (d) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Nishimura, H.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M.; Ogita, K.; Yoneda, Y. J. Med. Chem. 1994, 37, 3956-3968.
5. For recent reviews on tetrahydroquinolines, see: (a) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785. (b) Katritsky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070. See also: (c) Gilchrist, T. L.; Rahman, A. J. Chem. Soc., Perkin Trans. 1 1998, 1203-1207. (d) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Nishimura, H.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M.; Ogita, K.; Yoneda, Y. J. Med. Chem. 1994, 37, 3956-3968.
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7. For a recent review on benzoxazines, see: (a) Sainsbury, M. Rodd's Chem. Carbon Compd., 2nd ed.; Elsevier: Amsterdam, 1998; pp 465-511. See also: (b) Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyamoto, K.; Maruyama, N.; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. J. Med. Chem. 1997, 40, 105-111.
8. For reviews on quinoxalines, see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481-2515. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1978, 22, 367-431. See also (c) Awad, I. M. A. J. Chem. Technol. Biotechnol. 1992, 53, 227-236. (d) Kleim, J.-P.; Bender, R.; Billhardt, U.-M.; Meichsner, C.; Riess, G.; Rösner, M.; Winkler, I.; Paessens, A. Antimicrob. Agents Chemother. 1993, 37, 1659-1664. (e) Kleim, J.-P.; Rösner, M.; Winkler, I.; Paessens, A.; Kirsch, R.; Hsiou, Y.; Arnold, E.; Riess, G. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 34-38.
9. For reviews on quinoxalines, see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481-2515. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1978, 22, 367-431. See also (c) Awad, I. M. A. J. Chem. Technol. Biotechnol. 1992, 53, 227-236. (d) Kleim, J.-P.; Bender, R.; Billhardt, U.-M.; Meichsner, C.; Riess, G.; Rösner, M.; Winkler, I.; Paessens, A. Antimicrob. Agents Chemother. 1993, 37, 1659-1664. (e) Kleim, J.-P.; Rösner, M.; Winkler, I.; Paessens, A.; Kirsch, R.; Hsiou, Y.; Arnold, E.; Riess, G. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 34-38.
10. For reviews on quinoxalines, see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481-2515. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1978, 22, 367-431. See also (c) Awad, I. M. A. J. Chem. Technol. Biotechnol. 1992, 53, 227-236. (d) Kleim, J.-P.; Bender, R.; Billhardt, U.-M.; Meichsner, C.; Riess, G.; Rösner, M.; Winkler, I.; Paessens, A. Antimicrob. Agents Chemother. 1993, 37, 1659-1664. (e) Kleim, J.-P.; Rösner, M.; Winkler, I.; Paessens, A.; Kirsch, R.; Hsiou, Y.; Arnold, E.; Riess, G. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 34-38.
11. For reviews on quinoxalines, see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481-2515. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1978, 22, 367-431. See also (c) Awad, I. M. A. J. Chem. Technol. Biotechnol. 1992, 53, 227-236. (d) Kleim, J.-P.; Bender, R.; Billhardt, U.-M.; Meichsner, C.; Riess, G.; Rösner, M.; Winkler, I.; Paessens, A. Antimicrob. Agents Chemother. 1993, 37, 1659-1664. (e) Kleim, J.-P.; Rösner, M.; Winkler, I.; Paessens, A.; Kirsch, R.; Hsiou, Y.; Arnold, E.; Riess, G. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 34-38.
12. For reviews on quinoxalines, see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481-2515. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1978, 22, 367-431. See also (c) Awad, I. M. A. J. Chem. Technol. Biotechnol. 1992, 53, 227-236. (d) Kleim, J.-P.; Bender, R.; Billhardt, U.-M.; Meichsner, C.; Riess, G.; Rösner, M.; Winkler, I.; Paessens, A. Antimicrob. Agents Chemother. 1993, 37, 1659-1664. (e) Kleim, J.-P.; Rösner, M.; Winkler, I.; Paessens, A.; Kirsch, R.; Hsiou, Y.; Arnold, E.; Riess, G. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 34-38.
13. Reduction-reductive animation: (a) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; pp 82-93. (b) Artico, M.; DeMartino, G.; Filacchione, G. Giuliano, R. Farmaco, Ed. Sci. 1969, 24, 276-284; Chem Abstr. 1970, 70, 96775a.
14. Reduction-reductive animation: (a) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; pp 82-93. (b) Artico, M.; DeMartino, G.; Filacchione, G. Giuliano, R. Farmaco, Ed. Sci. 1969, 24, 276-284; Chem Abstr. 1970, 70, 96775a.
15. Reduction-reductive animation: (a) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; pp 82-93. (b) Artico, M.; DeMartino, G.; Filacchione, G. Giuliano, R. Farmaco, Ed. Sci. 1969, 24, 276-284; Chem Abstr. 1970, 70, 96775a.
16. Reduction-lactam formation: (a) Floyd, D. M.; Moquin, R. V.; Atwal, K. S.; Ahmed, S. Z.; Spergal, S. H.; Gougoutas, J. Z.; Malley, M. F. J. Org. Chem. 1990, 55, 5572-5579. (b) Tapia, R. A.; Centella, C. R.; Valderrama, J. A. Synth. Commun. 1999, 29, 2163-2168.
17. Reduction-lactam formation: (a) Floyd, D. M.; Moquin, R. V.; Atwal, K. S.; Ahmed, S. Z.; Spergal, S. H.; Gougoutas, J. Z.; Malley, M. F. J. Org. Chem. 1990, 55, 5572-5579. (b) Tapia, R. A.; Centella, C. R.; Valderrama, J. A. Synth. Commun. 1999, 29, 2163-2168.
18. For a survey of most of the methods for nitroarene reduction, see Hudlicky, M. Reductions in Organic Chemistry, 2nd ed.; American Chemical Society: Washington D.C., 1996.
19. The acid was esterified using MeOH/HCl (g); see: Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: New York, 1989; p 700.
20. Makosza, M.; Tyrala, A. Synth. Commun. 1986, 16, 419-423.
21. Bull D. J.; Fray, M. J.; Mackenny, M. C.; Malloy, K. A. Synlett 1996, 647-648.
22. Bunce, R. A.; Pierce, J. D. Org. Prep. Proced. Int. 1987, 19, 67-71.
23. Balsevich, J. Can. J. Chem. 1983, 61, 1053-1059.
24. See ref 8, p 986.
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26. Sunitha, K.; Balasubramanian, K. K. Tetrahedron 1987, 43, 3269-3278.
27. Attempts to perform the alkylation with ethyl (E)-4-bromo-2-butenoate in refluxing acetone resulted in alkylation and double-bond migration to give ethyl (Z)-4-(2-nitrophenyl)-3-butenoate. See: (a) Reference 15. (b) Balakumar, A.; Janardhanam, S.; Rajagopalan, K. Indian J. Chem. 1993, 32B, 313-317.
28. Attempts to perform the alkylation with ethyl (E)-4-bromo-2- butenoate in refluxing acetone resulted in alkylation and double-bond migration to give ethyl (Z)-4-(2-nitrophenyl)-3-butenoate. See: (a) Reference 15. (b) Balakumar, A.; Janardhanam, S.; Rajagopalan, K. Indian J. Chem. 1993, 32B, 313-317.
29. Safaryn, J. E.; Chiarello, J.; Chen, K.-M.; Joullie, M. M. Tetrahedron 1986, 42, 2635-2642.
30. 3OH) have been found to give predominantly the Z olefin; see: Valverde, S.; Martin-Lomas, M.; Herradon, B.; Garcia-Ochoa, S. Tetrahedron 1987, 43, 1895-1901. In the current procedure, the crude aldehyde contained some residual methanol from the ozonolysis reaction and DMSO from the reductive workup procedure.
31. Speziale, A. J.; Jaworski, E. G. J. Org. Chem. 1960, 25, 728-732.
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33. (a) Norman, R. O. C.; Coxon, J. M. Principles of Organic Synthesis, 3rd ed.; Chapman and Hall: New York, 1993; pp 666-668.
34. (b) Use of 3-5 equiv of iron gave less consistent yields.
35. See, for example: (a) Bunce, R. A.; Peeples, C. J.; Jones, P. B. J. Org. Chem. 1992, 57, 1727-1733. (b) Bunce, R. A.; Bennett, M. J. Synth. Commun. 1993, 23, 1009-1020.
36. See, for example: (a) Bunce, R. A.; Peeples, C. J.; Jones, P. B. J. Org. Chem. 1992, 57, 1727-1733. (b) Bunce, R. A.; Bennett, M. J. Synth. Commun. 1993, 23, 1009-1020.
37. For reductions using activated iron, see: (a) Hazlet, S. E.; Dornfeld, C. A. J. Am. Chem. Soc. 1944, 66, 1781-1782. (b) Eisch, J. J.; Kovacs, C. A.; Rhee, S.-G. J. Organomet. Chem. 1974, 65, 289- 301.
38. For reductions using activated iron, see: (a) Hazlet, S. E.; Dornfeld, C. A. J. Am. Chem. Soc. 1944, 66, 1781-1782. (b) Eisch, J. J.; Kovacs, C. A.; Rhee, S.-G. J. Organomet. Chem. 1974, 65, 289-301.
39. For reductions using iron in the presence of acids, see: (a) Reference 7. (b) West, R. W. J. Chem. Soc. 1925, 127, 494-495. (c) Wertheim, E. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, pp 471-473. (d) Mosby, W. L. J. Org. Chem. 1959, 24, 421-423. (e) Wulfman, D. S.; Cooper, C. F. Synthesis 1978, 924-925.
40. For reductions using iron in the presence of acids, see: (a) Reference 7. (b) West, R. W. J. Chem. Soc. 1925, 127, 494-495. (c) Wertheim, E. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, pp 471-473. (d) Mosby, W. L. J. Org. Chem. 1959, 24, 421-423. (e) Wulfman, D. S.; Cooper, C. F. Synthesis 1978, 924-925.
41. For reductions using iron in the presence of acids, see: (a) Reference 7. (b) West, R. W. J. Chem. Soc. 1925, 127, 494-495. (c) Wertheim, E. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, pp 471-473. (d) Mosby, W. L. J. Org. Chem. 1959, 24, 421-423. (e) Wulfman, D. S.; Cooper, C. F. Synthesis 1978, 924-925.
42. For reductions using iron in the presence of acids, see: (a) Reference 7. (b) West, R. W. J. Chem. Soc. 1925, 127, 494-495. (c) Wertheim, E. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, pp 471-473. (d) Mosby, W. L. J. Org. Chem. 1959, 24, 421-423. (e) Wulfman, D. S.; Cooper, C. F. Synthesis 1978, 924-925.
43. For reductions using iron in the presence of acids, see: (a) Reference 7. (b) West, R. W. J. Chem. Soc. 1925, 127, 494-495. (c) Wertheim, E. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, pp 471-473. (d) Mosby, W. L. J. Org. Chem. 1959, 24, 421-423. (e) Wulfman, D. S.; Cooper, C. F. Synthesis 1978, 924-925.
44. Other mild conditions for nitroarene reductions have also been reported, but were not investigated for the current reaction; see: (a) Alper, H.; Gopal, M. J. Chem. Soc., Chem. Commun. 1980, 821. (b) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1990, 31, 4065-4066. (c) Baruah, R. N. Indian J. Chem. 1994, 33B, 758. (d) Desai, D. G.; Swami, S. S.; Hapase, S. B. Synth. Commun. 1999, 29, 1033-1036. (e) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
45. Other mild conditions for nitroarene reductions have also been reported, but were not investigated for the current reaction; see: (a) Alper, H.; Gopal, M. J. Chem. Soc., Chem. Commun. 1980, 821. (b) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1990, 31, 4065-4066. (c) Baruah, R. N. Indian J. Chem. 1994, 33B, 758. (d) Desai, D. G.; Swami, S. S.; Hapase, S. B. Synth. Commun. 1999, 29, 1033-1036. (e) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
46. Other mild conditions for nitroarene reductions have also been reported, but were not investigated for the current reaction; see: (a) Alper, H.; Gopal, M. J. Chem. Soc., Chem. Commun. 1980, 821. (b) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1990, 31, 4065-4066. (c) Baruah, R. N. Indian J. Chem. 1994, 33B, 758. (d) Desai, D. G.; Swami, S. S.; Hapase, S. B. Synth. Commun. 1999, 29, 1033-1036. (e) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
47. Other mild conditions for nitroarene reductions have also been reported, but were not investigated for the current reaction; see: (a) Alper, H.; Gopal, M. J. Chem. Soc., Chem. Commun. 1980, 821. (b) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1990, 31, 4065-4066. (c) Baruah, R. N. Indian J. Chem. 1994, 33B, 758. (d) Desai, D. G.; Swami, S. S.; Hapase, S. B. Synth. Commun. 1999, 29, 1033-1036. (e) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
48. Other mild conditions for nitroarene reductions have also been reported, but were not investigated for the current reaction; see: (a) Alper, H.; Gopal, M. J. Chem. Soc., Chem. Commun. 1980, 821. (b) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1990, 31, 4065-4066. (c) Baruah, R. N. Indian J. Chem. 1994, 33B, 758. (d) Desai, D. G.; Swami, S. S.; Hapase, S. B. Synth. Commun. 1999, 29, 1033-1036. (e) Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2777-2779.
49. For reductions using iron in the presence of added salts, see: (a) Lyons, R. E.; Smith, L. T. Chem. Ber. 1927, 60, 173-182. (b) Hodgson, H. H.; Whitehurst, J. S. J. Chem. Soc. 1945, 202-204. (c) Senkus, M. Ind. Eng. Chem. 1948, 40, 506-508.
50. For reductions using iron in the presence of added salts, see: (a) Lyons, R. E.; Smith, L. T. Chem. Ber. 1927, 60, 173-182. (b) Hodgson, H. H.; Whitehurst, J. S. J. Chem. Soc. 1945, 202-204. (c) Senkus, M. Ind. Eng. Chem. 1948, 40, 506-508.
51. For reductions using iron in the presence of added salts, see: (a) Lyons, R. E.; Smith, L. T. Chem. Ber. 1927, 60, 173-182. (b) Hodgson, H. H.; Whitehurst, J. S. J. Chem. Soc. 1945, 202-204. (c) Senkus, M. Ind. Eng. Chem. 1948, 40, 506-508.
52. 2O (0.25 mmol/4.00 mL) was found to have a pH of 4. This appears to be sufficiently acidic to slowly cleave the allylic ethers.
53. (a) Grandmougin, E. Chem Ber. 1906, 39, 3561-3564.
54. (b) Fieser, L. F.; Fieser, M. J. Am. Chem. Soc. 1934, 56, 1565-1578.