A convenient regioselective synthesis of pyrano[3,2-b]acridones involving nucleophilic addition to benzyne

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 7003-7006

  Rudas, Mónika ^a   Nyerges, Miklós ^a   Töke, László ^a   Pete, Béla ^a   Groundwater, Paul W ^b  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b UNIVERSITY OF SUNDERLAND   (United Kingdom)

Author keywords

Acridines; Alkaloids; Arynes; Pyrones

Indexed keywords

ACRIDINE DERIVATIVE; ACRIDONE DERIVATIVE; ALKALOID; BENZENE DERIVATIVE; ESTER DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033578886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01424-0     Document Type: Article

References (17)

1. Ju-ichi, M.; Inoue, M.; Sakiyama, K.; Yoneda, M.; Furukawa, H. Heterocycles 1987, 26, 2057.
2. Furukawa, H.; Ito, C.; Mizuno, T.; Ju-ichi, M.; Inoue, M.; Kaijura, I.; Omura, M. J. Chem. Soc., Perkin Trans, 1 1990, 1593.
3. Takemura, J.; Uchida, H.; Ju-ichi, M.; Ito, C.; Nakagawa, K.; Ono, T.; Furukawa, H. Heterocycles 1992, 34, 2123.
4. Reisch, J.; Hearth, H. M. T. B.; Kumar, N. S. Liebigs Ann. Chem. 1991, 685.
5. Groundwater, P. W.; Munawar, M. A.. In Adv. in Heterocyclic Chem.; Ed. Katritzky A. R.; Academic Press, 1998, 70, 89.
6. (a) Groundwater, P. W.; Solomons, K. R. H.. J.Chem.Soc., Perkin Trans. 1. 1994, 173.
7. (b) Drewe, J. A.; Groundwater P. W. J.Chem.Soc., Perkin Trans. 1, 1997, 601.
8. Kotali, A.; Harris, P. A.. Org. Prep. Proc. Int. 1994, 26, 159.
9. Baker, S.; Crombie L.; Dove, R.V.; Slack, D.A. J. Chem. Soc. Perkin Trans 1. 1979, 677.
10. Kessar, S.V. Comprehensive Org. Synth. Eds. B. M. Trost and I. Fleming; Pergamon Press, 1991, Vol.4; pp.483.
11. Benzyne precursors have been utilised for the synthesis of some simple acridone derivatives and acronycine itself. In these cases the less sensitive substituent pattern allowed the generation of arynes from the corresponding halogen using strong base. See for example; Watanabe, M.; Kurosaki, A.; Furukawa, S. Chem. Pharm. Bull. 1984, 32, 1264.
12. Baker, W. J. Chem. Soc. 1933, 1381.
13. Durga Nath Dhar; The Chemistry of Chalcones and Related Compounds; John Wiley & Sons, 1981.
14. 6) 11.96 (1H, s, NH), 9.96 (1H, s, OH), 8.89 (1H, s, H-12 ), 8.22 (1H, d, J 7.5 Hz, H-10), 7.77 (1H, t, J 8.3 Hz, H-8), 7.64 (1H, dd, J 8.3 Hz, J 2.2 Hz, Ar-6′), 7.61 (1H, d, J 2.2 Hz, Ar-2′), 7.59 (1H, s, H-5), 7.53 (1H, d, J 8.3 Hz, H-7), 7.30 (1H, t, J 7.5 Hz, H-9), 6.98 (1H, d, J 8.3 Hz, Ar-5′), 6.93 (1H, s, H-2), 3.93 (3H, s, OMe).
15. Silva, A. M.S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1994, 35, 5899.
16. Wang, D. L.; Imafuku, K. J. Net. Chem. 1998, 35, 1413.
17. 6) 8.28 (1H, d, J 7.5 Hz, H-10), 8.02 (1H, s, H-12), 7.76 (2H, m, H-7 and H-8), 7.29 (1H, t, J 7.5 Hz, H-9), 7.08 (1H, s, H-5), 6.62 (1H, d, J 10 Hz, H-1), 5.86 (1H, d, J 10 Hz, H-2), 3.81 (3H, s, NMe), 1.45 (6H, s, 2 × Me)