Dihydrobenzoxazines and Tetrahydroquinoxalines by a Tandem Reduction-Reductive Amination Reaction

Journal of Heterocyclic Chemistry

Volumn 40, Issue 6, 2003, Pages 1031-1039

  Bunce, Richard A ^a   Herron, Derrick M ^a   Hale, Lu Y ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 1,2,3,4 TETRAHYDROQUINOXALINE; 2 FLUORO 1 NITROBENZENE; 2 NITROACETANILIDE; 2 NITROPHENOL; 3,4 DIHYDRO 2H 1,4 BENZOXAZINE; ACETANILIDE DERIVATIVE; ALLYLIC HALIDE; ANION; BENZOXAZINE DERIVATIVE; CARBON; DIHYDROBENZOXAZINE; FORMALDEHYDE; HALIDE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; METHANOL; NITROGEN; NITROKETONE; PALLADIUM; QUINOXALINE DERIVATIVE; TETRAHYDROQUINOXALINE; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CHROMATOGRAPHY; CYCLIZATION; HYDROGENATION; OZONOLYSIS; REDUCTION; RING CLOSING METATHESIS; SYNTHESIS; TANDEM REDUCTION REDUCTIVE AMINATION REACTION;

EID: 0347087382     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400611     Document Type: Article

References (44)

1. Undergraduate research participant, 1999-2003.
2. [2a] R. A. Bunce, D. M. Herron, L. B. Johnson and S. V. Kotturi, J. Org. Chem., 66, 2822 (2001);
3. [b] R. A. Bunce, D. M. Herron, J. R. Lewis, S. V. Kotturi and E. M. Holt, J. Heterocyclic Chem., 40, 101 (2003);
4. [c] R. A. Bunce, D. M. Herron, J. R. Lewis and S. V. Kotturi, J. Heterocyclic Chem., 40, 113 (2003).
5. For earlier syntheses of 3,4-dihydro-2H-1,4-benzoxazines, see [a] G. Barker, G. P. Ellis and D. A. Wilson, J. Chem. Soc. (C), 2079 (1971);
6. [b] R. Fusco, L. Garanti and G. Zecchi, J. Org. Chem., 40, 1906 (1975);
7. [c] H. Bartsch, W. Kropp and M. Pailer, Monatsch. Chem., 110, 257 (1979);
8. [d] P. Battistoni, P. Bruni and G. Fava, Synthesis, 220 (1979);
9. [e] G. Coudert, G. Guillaumet and B. Loubinoux, Synthesis, 541 (1979);
10. [f] S. Kotha, V. Bindra and A. Kuki, Heterocycles, 38, 5 (1994);
11. [g] J. M. Flaniken, C. J. Collins, M. Lanz and B. Singaram, Org. Lett., 1, 799 (1999);
12. [h] S. Kuwabe, K. E. Torraca and S. L. Buchwald, J. Am. Chem. Soc., 123, 12202 (2001).
13. For earlier syntheses of 1,2,3,4-tetrahydroquinoxalines, see [a] J. C. Cavagnol and F. Y. Wiselogle, J. Am. Chem. Soc., 69, 795 (1947);
14. [b] J. S. Morley, J. Chem. Soc., 4002 (1952);
15. [c] R. F. Smith, W. J. Rebel and T. N. Beach, J. Org. Chem., 24, 205 (1959);
16. [d] J. Figueras, J. Org. Chem., 31, 803 (1966);
17. [e] G. H. Fisher and H. P. Schultz, J. Org. Chem., 39, 635 (1974);
18. [f] T. O. Olagbemiro, C. A. Nyakutse, L. Lajide, M. O. Agho and C. E. Chukwu, Bull. Chim. Soc. Belg., 96, 473 (1987);
19. [g] T. Renaud, J.-P. Hurvois and P. Uriac, Eur. J. Org. Chem., 987 (2001).
20. T. Kuroita, M. Sakamori and T. Kawakita, Chem. Pharm. Bull., 44, 756 (1996).
21. M. Kajino, Y. Shibouta, K. Nishikawa and K. Meguro, Chem. Pharm. Bull., 39, 2896 (1991).
22. [7a] M. Largeron, B. Lockhart, B. Pfeiffer and M.-B. Fleury, J. Med. Chem., 42, 5043 (1999);
23. [b] M. Largeron, B. Mesples, P. Gressens, R. Cecchelli, M. Spedding, A. Le Ridant and M.-B. Fleury, Eur. J. Pharmacol., 424, 189 (2001).
24. L. Landriani, D. Barlocco, G. Cignarella, M. M. Curzu, V. Anania and M. S. Desole, Farm. Ed. Sci., 42, 191 (1987); Chem. Abstr., 107, 51381 (1987).
25. L. Landriani, D. Barlocco, G. Cignarella, M. M. Curzu, V. Anania and M. S. Desole, Farm. Ed. Sci., 42, 191 (1987); Chem. Abstr., 107, 51381 (1987).
26. J.-D. Bourzat, A. Commercon, B. J. C. Filoche, N. V. Harris, T. D. Pallin and K. A. J. Stuttle, Patent WO 0039103 (2000); Chem. Abstr., 133, 89546 (2000).
27. J.-D. Bourzat, A. Commercon, B. J. C. Filoche, N. V. Harris, T. D. Pallin and K. A. J. Stuttle, Patent WO 0039103 (2000); Chem. Abstr., 133, 89546 (2000).
28. J. B. Gale, J. Klucik, S. Subramanian and K. D. Berlin, Org. Prep. Proced. Int., 33, 487 (2001). This paper reports the synthesis of 2-allyloxy-1-nitrobenzene in 56% yield from allyl bromide and 2-nitrophenol using sodium hydroxide in water. We obtained a 90% yield when the reaction was run using sodium hydride in N,N-dimethylformamide.
29. [11a] R. A. Bunce and K. M. Easton, Org. Prep. Proced. Int., submitted;
30. See also [b] T. F. Woiwode, C. Rose and T. J. Wandless, J. Org. Chem., 63, 9594 (1998);
31. [c] S. Raeppel, F. Raeppel and J. Suffert, Synlett, 794 (1998).
32. Reactions of allylic halides with aniline typically require the use of excess aniline to prevent multiple alkylations.
33. A very minor amount (2-3%) of the products from N-methylation of 28 and 30 were also detected.
34. [14a] L. Mandolini, Adv. Phys. Org. Chem., 22, 1 (1986);
35. [b] G. Illuminati and L. Mandolini, Acct. Chem. Res., 14, 95 (1981);
36. [c] D. F. DeTar and N. P. Luthra, J. Am. Chem. Soc., 102, 4505 (1980).
37. W. C. Stille, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).
38. This alcohol was prepared in two steps from 1-hexyne. Step 1: Markovnikov addition of hydrogen bromide to 1-hexyne, see J. Cousseau, Synthesis, 805 (1980). Step 2: Grignard reaction of the resulting 2-bromo-1-hexene with formaldehyde.
39. The 2-phenyl-2-propen-1-ol used in this procedure was prepared by the method described in H. E. Zimmerman and R. A. Bunce, J. Org. Chem., 47, 3377 (1982).
40. R. J. Fletcher, C. Lampard, J. A. Murphy and N. Lewis, J. Chem Soc., Perkin Trans. 1, 623 (1995).
41. The bromide was prepared in two steps from 1-cyclopentene-1-carboxaldehyde, see J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 3634 (1950). Step 1: Reduction of the aldehyde with lithium aluminum hydride. Step 2: Conversion of the resulting alcohol to the bromide with phosphorus tribromide, see L. Borowiecki and A. Kazubski, Pol. J. Chem., 52, 1447 (1978).
42. The bromide was prepared in two steps from 1-cyclopentene-1-carboxaldehyde, see J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 3634 (1950). Step 1: Reduction of the aldehyde with lithium aluminum hydride. Step 2: Conversion of the resulting alcohol to the bromide with phosphorus tribromide, see L. Borowiecki and A. Kazubski, Pol. J. Chem., 52, 1447 (1978).
43. A. L. J. Beckwith and G. F. Meijs, J. Org. Chem., 52, 1922 (1987).
44. The 3-bromo-2-phenyl-l-propene used in this procedure was prepared by reaction of 2-phenyl-2-propen-1-ol [17] with phosphorus tribromide [19]. The crude bromide was used without purification.