Microwave-assisted solid-phase Dötz benzannulation reaction: A facile synthesis of 2,3-disubstituted-1,4-naphthoquinones

Tetrahedron Letters

Volumn 46, Issue 44, 2005, Pages 7545-7548

  Shanmugasundaram, Muthian ^a   Garcia Martinez, Israel ^a   Li, Qingyi ^a   Estrada, Abril ^a   Martinez, Nancy E ^a   Martinez, Luis E ^a  

^a UNIVERSITY OF TEXAS AT EL PASO   (United States)

Author keywords

1,4 Naphthoquinones; D tz reaction; Fischer carbenes; Microwave; Solid phase synthesis

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALKYNE; CARBENE; CHROMIUM DERIVATIVE; NAPHTHOL DERIVATIVE; RESIN;

ANNULATION REACTION; ARTICLE; DOTZ BENZANNULATION; DRUG PURITY; GAS CHROMATOGRAPHY; MICROWAVE IRRADIATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS;

EID: 26244462184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.158     Document Type: Article

References (39)

1. R.E. Sammelson, and M.J. Kurth Chem. Rev. 101 2001 137
2. B.A. Lorsbach, and M.J. Kurth Chem. Rev. 99 1999 1549
3. C.J. Andres, D.L. Whitehouse, and M.S. Deshpande Curr. Opin. Chem. Biol. 2 1998 353
4. K.H. Dötz Angew. Chem., Int. Ed. Engl. 14 1975 644
5. K.H. Dötz Pure Appl. Chem. 55 1983 1689
6. K.H. Dötz Angew. Chem., Int. Ed. Engl. 23 1984 587
7. W.D. Wulff E.W. Abel F.G.A. Stone G. Wilkinson L.S. Hegedus Comprehensive Organometallic Chemistry II Vol. 12 1995 Pergamon Oxford 469 547
8. W.D. Wulff B.M. Trost I. Flemming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 1065 1113
9. A. de Meijere, H. Schirmer, and M. Duetsch Angew. Chem., Int. Ed. 39 2000 3964
10. J.W. Herndon Tetrahedron 56 2000 1257
11. M. Gómez-Gallego, M.J. Mañcheno, and M.A. Sierra Acc. Chem. Res. 38 2005 44
12. A. Yamashita Tetrahedron Lett. 27 1986 5915
13. K.S. Chan, G.A. Peterson, T.A. Brandvold, K.L. Faron, C.A. Challener, C. Hyldahl, and W.D. Wulff J. Organomet. Chem. 334 1987 9
14. M.E. Bos, W.D. Wulff, R.A. Miller, S. Chamberlin, and T.A. Brandvold J. Am. Chem. Soc. 113 1991 9293
15. M.L. Waters, M.E. Bos, and W.D. Wulff J. Am. Chem. Soc. 121 1999 6403
16. S. Maiorana, P. Seneci, T. Rossi, C. Baldoli, M. Ciraco, E. de Magistris, E. Licandro, A. Papagni, and S. Provera Tetrahedron Lett. 40 1999 3635
17. S. Klapdohr, K.H. Dötz, W. Assenmacher, W. Hoffbauer, N. Hüsing, M. Nieger, J. Pfeiffer, M. Popall, U. Schubert, and G. Trimmel Chem. Eur. J. 6 2000 3006
18. S.R. Pulley, and L.S. Hegedus J. Am. Chem. Soc. 115 1993 9037
19. J.A. Connor, and E.M. Jones J. Chem. Soc. A 1971 1974
20. J.A. Connor, and E.M. Jones J. Chem. Soc., Chem. Commun. 1971 570
21. B.C. Söderberg, and L.S. Hegedus Organometallics 9 1990 3113
22. B.C. Söderberg, L.S. Hegedus, and M.A. Sierra J. Am. Chem. Soc. 112 1990 4364
23. -1. (Found: Cr, 5.67%. 95% loading @ 1.7 mmol/g requires Cr, 5.99%).
24. J.S. McCallum, F.A. Kunng, S.R. Gilbertson, and W.D. Wulff Organometallics 7 1988 2346
25. A. Hafner, L.S. Hegedus, G. deWeck, B. Hawkins, and K.H. Dötz J. Am. Chem. Soc. 110 1988 8413
26. E.J. Hutchinson, W.J. Kerr, and E.J. Magennis Chem. Commun. 2002 2262
27. 4 and filtered. The solvent was removed under vacuum to afford pure 1,4-naphthoquinones 5a-l.
28. C.F. Bernasconi, F.X. Flores, and K.W. Kittredge J. Am. Chem. Soc. 119 1997 2103
29. some of the references: R.B. Silverman, and R.A. Ologson J. Chem. Soc., Chem. Commun. 1968 1313
30. E.O. Fischer, and S. Riedmüller Chem. Ber. 107 1974 915
31. C.P. Casey, and W.R. Brunsvold J. Organomet. Chem. 102 1975 175
32. J. Barluenga, A.A. Trabanco, J. Flórez, S. Garcia-Granda, and E. Martin J. Am. Chem. Soc. 118 1996 13099
33. N. Kongakathip, B. Kongakathip, P. Siripong, C. Sangma, S. Luangkamin, M. Niyomdecha, S. Pattanapa, S. Piyaviriyagul, and P. Konggaeree Biorg. Med. Chem. 11 2003 3179
34. J. Bao, W.D. Wulff, M.J. Fumo, E.B. Grant, D.P. Heller, M.C. Whitcomb, and S.-M. Yeung J. Am. Chem. Soc. 118 1996 2166
35. R.H. Thompson Naturally Occurring Quinones 2nd ed. 1971 Academic Press London and New York
36. Y. Naruta, and J. Maruyama Recent Advances in the Synthesis of Quinoid Compounds S. Patai Z. Rappoport The Chemistry of Quinoid Compounds Vol. II 1988 Wiley New York 24
37. J. Montoya, A. Varela-Ramirez, M. Shanmugasundaram, L.E. Martinez, T.P. Primm, and R.J. Aguilera Biochem. Biophys. Res. Commun. 335 2005 367
38. J. Montoya, A. Varela-Ramirez, A. Estrada, L.E. Martinez, K. Garza, and R.J. Aguilera Biochem. Biophys. Res. Commun. 325 2004 1517
39. T. Tran, E. Saheba, A.V. Arcerio, V. Chavez, Q.-Y. Li, L.E. Martinez, and T.P. Primm Biorg. Med. Chem. 12 2004 4809