Aryl radical cyclization: Regioselective synthesis of 6a,7,8,12b- tetrahydro-6H-chromeno[3,4-c]quinolin-6-one

Synthetic Communications

Volumn 38, Issue 11, 2008, Pages 1768-1777

  Majumdar, K C ^a   Debnath, P ^a   Chottopadhyay, S K ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

6 endo trig; Aryl radical cyclization; Coumarin derivatives; Organotin reagent; Tetrahydroquinolines

Indexed keywords

2 BROMOANILINE; 3 (2 BROMOANILINOMETHYL)COUMARIN; 3 CHLOROMETHYL COUMARIN; 6ALPHA,7,8,12BETA TETRAHYDRO 6H CHROMENO[3,4 C]QUINOLIN 6 ONE; COUMARIN DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 45749127504     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801982191     Document Type: Article

References (37)

1. (a) Coumarin biological activities: For an extensive bibliography, see Wu, J.; Liao, Y.; Yang, Z. Synthesis of 4-substituted coumarins via the palladium-catalyzed cross-coupling of 4-tosylcoumarins with terminal acetylenes and organozinc reagents. J. Org. Chem. 2001, 66, 3642;
2. (b) Dean, F. M. Naturally Occurring Oxygen Ring Compounds; Butterworths: London, 1963;
3. (c) Murray, D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry and Biochemistry; J. Wiley & Sons: New York, 1982.
4. (a) Raski, S. R.; Williams, R. M. DNA cross-linking agents as antitumor drugs. Chem. Rev. 1998, 98, 2723;
5. (b) Murakami, A.; Gao, G.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Takahasi, D.; Koshimizu, K.; Ohigashi, H. 1,1-Dimethylallylcoumarins potently supress both lipopolysaccharide- and interferon-γ-induced nitric oxide generation in mouse macrophage RAW 264.7 cells. Bioorg. Med. Chem. Lett. 2000, 10, 59;
6. (c) Guilet, D.; Helesbeux, J. J.; Seraphin, D.; Sevenet, T.; Richomme, P.; Bruneton, J. Novel cytotoxic 4-phenylfuranocoumarins from Calophyllum dispar. J. Nat. Prod. 2001, 64, 563;
7. (d) Kang, S. Y.; Lee, K. Y.; Sung, S. H.; Park, M. J.; Kim, Y. C. Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: Structure-activity relationships. J. Nat. Prod. 2001, 64, 683;
8. (e) Feuer, G. In Progress in Medicinal Chemistry; Ellis, G. P. and West, G. B., Eds.; North-Holland Publishing Compeny: New York, 1974;
9. (f ) Audus, L. J.; Quastel, J. H. Coumarin as a selective phytocidal agent. Nature 1947, 159, 320.
10. (a) Ukawa, K.; Ishiguro, T.; Wada, Y.; Nohara, A. Synthesis of 5-oxo-5H-[1]benzopyrano[4,3-b]pyridine derivatives. Heterocycles 1986, 24, 1931;
11. (b) Heber, D. Reactions at heterocyclen with 2-acyl-2-propenon- teilstruktur; 3; Memo, pyrido [3,2-c] cumarine from 3-substituierten 1-Benzopyranen and Enaminen. Arch. Pharm. 1987, 320, 402;
12. (c) Heber, D.; Berghaus, T. Synthesis of 5H [1] benzopyrano [4,3-b] pyridin-5-ones containing an azacannabinoidal structure. J. Heterocycl. Chem. 1994, 31, 1353.
13. (a) Trecourt, F.; Marsais, F.; Gungor, T.; Queguiner, G. Improved synthesis of 2,3-disubstituted pyridines by metallation of 2-chloropyridine: A convenient route to fused polyheterocycles. J. Chem. Soc., Perkin Trans. 1 1990, 2409;
14. (b) Yavari, I.; Adib, M.; Hojabri, L. Vinyltriphenylphosphonium salt mediated synthesis of 1,4-benzoxazine and coumarin derivatives. Tetrahedron 2002, 58, 6895;
15. (c) Billeret, D.; Blondeau, D.; Silwa, H. Convenient synthesis of 5-azacoumarins. J. Heterocycl. Chem. 1993, 30, 671.
16. Galariniotou, E.; Fragos, V.; Makri, A.; Litinas, K. E.; Nicolaides, D. N. Synthesis of novel pyridocoumarins and benzo-fused 6-azacoumarins. Tetrahedron 2007, 63, 8298.
17. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986;
18. (b) Renaud, P.; Sibi, M. P. Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol. 1;
19. (c) Malacria, M. Selective preparation of complex polycyclic molecules from acyclic precursors via radical mediated- or transition metal-catalyzed cascade reactions. Chem. Rev. 1996, 96, 289;
20. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Radical reactions in natural product synthesis. Chem. Rev. 1991, 91, 1237;
21. (e) Majumdar, K. C.; Basu, P. K. Formation of five- and six-membered heterocyclic rings by radical cyclization. Heterocycles 2002, 57, 2413;
22. (f) Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P. P. Fomation of five- and six-membered heterocyclic rings under radical cyclization conditions. Tetrahedron 2004, 60, 6239;
23. (g) Majumdar, K. C.; Alam, S. Regioselective unusual formation of spirocyclic 4-{2′-benzo(2′,3′-dihydro)furo}-9-methyl-2,3,9- trihydrothiopyrano[2,3-b]indole by 4-exo-trig aryl radical cyclization and rearrangement. Org. Lett. 2006, 8, 4059;
24. (h) Majumdar, K. C.; Basu, P. K.; Chattopadhyay, S. K. Fomation of five- and six-membered heterocyclic rings under radical cyclization conditions. Tetrahedron 2007, 63, 793.
25. (a) Bowman, W. R.; Bridge, C. F.; Brookes, P. Synthesis of heterocycles by radical cyclisation. J. Chem. Soc., Perkin Trans. 1 2000, 1;
26. (b) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. Synthesis of heterocycles by radical cyclisation. J. Chem. Soc., Perkin Trans. 1 2001, 2885;
27. (c) Kappe, T.; Kappe, C. O. In Progress in Heterocyclic Chemistry; Suschitzky, H. and Gribble, G., Eds.; Elsevier Science: New York, 1996; Vol. 8;
28. (d) Aldabbagh, F.; Bowman, W. R. Synthesis of heterocycles by radical cyclisation. Contemp. Org. Synth. 1997, 4, 261;
29. (e) Navarro-Vazquez, A.; Garcia, A.; Dominguez, D. A study of aryl radical cyclizatior. J. Org. Chem. 2002, 67, 3213, and references therein.
30. Majumdar, K. C.; Debnath, P.; Maji, P. K. Thiophenol-catalyzed Claisen rearrangement and radical cyclization: Formation of furo- and pyrano coumarin derivatives. Tetrahedron Lett. 2007, 48, 5265.
31. 3 mediated radical cyclization of 3-(o-bromophenoxymethyl) coumarins. Tetrahedron Lett. 2004, 45, 6871.
32. Majumdar, K. C.; Mukhopadhyay, P. P.; Biswas, A. Regioselective synthesis of quinolone-annulated sulfur heterocycles by aryl radical cyclisation. Tetrahedron Lett. 2005, 46, 6655.
33. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. Consecutive ring closure and neophyl rearrangement of some alkenylaryl redicals. J. Org. Chem. 1987, 52, 4072.
34. Ishibashi, H.; Kobayashi, T.; Nakashima, S.; Tamura, O. Regiochemistry in aryl radical cyclization onto methylenecycloalkanes. J. Org. Chem. 2000, 65, 9022.
35. (a) Spellmeyer, D. C.; Houk, K. N. Force-field model for intramolecular radical additions. J. Org. Chem. 1987, 52, 959;
36. (b) Beckwith, A. L. J.; Schiesser, C. H. Regio- and stereo-selectivity of alkenyl radical ring closure: A theoretical study. Tetrahedron 1985, 41, 3925;
37. (c) Giese, B. Formation of C-C bonds by addition of free radicals to alkenes. Angew. Chem. Int. Ed. 1983, 22, 753.