Efficient synthesis of pyrano[2,3-c]coumarins via intramolecular domino Knoevenagel hetero-Diels-Alder reactions

Tetrahedron

Volumn 65, Issue 21, 2009, Pages 4228-4234

  Khoshkholgh, Malihe Javan ^a   Lotfi, Minoo ^a   Balalaie, Saeed ^a   Rominger, Frank ^b  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Copper catalysis; Cycloadditions; Domino reactions; Oxygen heterocycles

Indexed keywords

4 HYDROXYCOUMARIN DERIVATIVE; COPPER; LEWIS ACID; PYRANO[2,3 C]CHROMONE; PYRANO[2,3 C]COUMARIN; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

ALNUS;

EID: 64649083781     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.032     Document Type: Article

References (43)

1. Boulton A.J., and Mckillop A. Comprehensive Heterocyclic Chemistry (1984), Pergamon, New York, NY
2. Norcross R.D., and Paterson I. Chem. Rev. 95 (1995) 2041-2114
3. Faulkner D.J. Nat. Prod. Rep. 14 (1997) 259-302
4. Danishefsky S.J. Aldrichimica Acta 19 (1986) 59-68
5. Schmidt R.R. Acc. Chem. Res. 19 (1986) 250-259
6. Payne D.J., Hueso-Rodríguez J.A., Boyd H., Concha N.O., Janson C.A., Gilpin M., Bateson J.H., Cheever C., Niconovich N.L., Pearson S., Rittenhouse S., Tew D., Díez E., Pérez P., de La Fuente J., Rees M., and Rivera-Sagredo A. Antimicrob. Agents Chemother. 46 (2002) 1880-1886
7. Dean F.M. Naturally Occurring Oxygen Ring Compounds (1963), Butterworths, London
8. Tietze L.F. Domino Reaction in Organic Synthesis (2006), Wiley-VCH, Weinheim
9. Chapman C.J., and Frost C.G. Synthesis (2007) 1-21
10. Enders D., Grondal C., and Hüttl M.R.M. Angew. Chem., Int. Ed. 46 (2007) 1570-1581
11. Tietze L.F. Chem. Rev. 96 (1996) 115-136
12. Gaddam V., and Nagarajan R. J. Org. Chem. 72 (2007) 3573-3576
13. Chebanov V.A., Saraev V.E., Desenko S., Chernenko V.N., Shishkina S.V., Chishkin O.V., Kobzar K.M., and Kappe C.O. Org. Lett. 9 (2007) 1691-1694
14. Tietze L.F., and Rackelman N. In: Zhu J., and Bienaymé H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim 121-167
15. Tietze L.F., and Rackelman N. Pure Appl. Chem. 76 (2004) 1967-1983
16. Tietze L.F. J. Heterocycl. Chem. 27 (1990) 47-69
17. Tietze L.F., Rackelman N., and Müller I. Chem.-Eur. J 10 (2004) 2722-2731
18. Yadav J.S., Reddy B.V.S., Narsimhaswamy D., Lakahmi P.N., Narsimulu K., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 45 (2004) 3493-3497
19. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 47 (2006) 2265-2270
20. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180-3211
21. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271-2296
22. Asao N., Sato K., and Yamamoto Y. J. Org. Chem. 70 (2005) 3682-3685
23. Asao N., Yudha S., Nogami T., and Yamamoto Y. Angew. Chem., Int. Ed. 44 (2005) 5526-5528
24. Ermolat D.S., Mehta V.P., and Eycken E.V.V. Synlett (2007) 3117-3122
25. Wender P.A., Paxton T.J., and Williams T.J. J. Am. Chem. Soc. 128 (2006) 14814-14815
26. Michelet V., Toullea P.Y., and Genêt J.-P. Angew. Chem., Int. Ed 47 (2008) 4268-4315
27. Asao N., Takahashi K., Lee S., Kasahara T., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 12650-12651
28. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079-3160
29. Asao N., Kasahara T., and Yamamoto Y. Angew. Chem., Int. Ed. 42 (2003) 3504-3506
30. Kamijo S., Sasaki Y., and Yamamoto Y. Tetrahedron Lett. 45 (2004) 35-38
31. Liu X.-Y., and Che C.-N. Angew. Chem., Int. Ed. 47 (2008) 3805-3810
32. Bi H.-P., Guo L.-N., Gou F.-R., Duan X.-H., Liu X.-Y., and Liang Y.-M. J. Org. Chem. 73 (2008) 4713-4716
33. Chen C., and Dormer P.G. J. Org. Chem. 70 (2005) 6964-6967
34. Evindar G., and Batey R. J. Org. Chem. 71 (2006) 1802-1808
35. Zhu W., and Ma D. Chem. Commun. (2004) 888-889
36. Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 14844-14845
37. Sreedhar B., Reddy P.S., and Kumar N.S. Tetrahedron Lett. 47 (2006) 3055-3058
38. Bock V.D., Hiemstra H., and Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68
39. Black D.A., and Arndtsen B.A. Org. Lett. 6 (2004) 1107-1110
40. Khoshkholgh M.J., Balalaie S., Gleiter R., and Rominger F. Tetrahedron 64 (2008) 10924-10929
41. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., Rominger F., and Gross J.H. Tetrahedron Lett. 49 (2008) 6965-6968
42. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. ARKIVOC ix (2009) 114-121
43. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. Synlett (2009) 55-58