A novel oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles

Tetrahedron

Volumn 63, Issue 39, 2007, Pages 9712-9717

  Chuang, Che Ping ^a   Tsai, An I ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

2 Amino 1,4 benzoquinones; Benzoylacetonitriles; Free radical; Manganese(III) acetate; Regioselectivity

Indexed keywords

ACETIC ACID; ACETONITRILE DERIVATIVE; BENZOQUINONE DERIVATIVE; FREE RADICAL; MANGANESE; SPIRO COMPOUND; SPIRONOLACTONE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; OXIDATION KINETICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 34547765857     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.008     Document Type: Article

References (52)

1. Hart D.J. Science 223 (1984) 883
2. Neumann W.P. Synthesis (1987) 665
3. Curran D.P. Synthesis (1988) 417 and 489
4. Melikyan G.G. Synthesis (1993) 833
5. Iqbal J., Bhatia B., and Nayyar N.K. Chem. Rev. 94 (1994) 519
6. Snider B.B. Chem. Rev. 96 (1996) 339
7. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Functional Groups: The Chemistry of the Quinoid Compounds (1988), Wiley, New York, NY
8. Thomson R.H. Naturally Occurring Quinones IV: Recent Advances (1997), Chapman and Hall, London
9. Shaw K.J., Luly J.R., and Rapoport H. J. Org. Chem. 50 (1985) 4515
10. Murphy W.S., and O'Sullivan P.J. Tetrahedron Lett. 33 (1992) 531
11. O'Sullivan P.J., Moreno R., and Murphy W.S. Tetrahedron Lett. 33 (1992) 535
12. Yogo M., Ito C., and Furukawa H. Chem. Pharm. Bull. 39 (1991) 328
13. Bittner S., Krief P., and Massil T. Synthesis (1991) 215
14. Knölker H.-J., and O'Sullivan N. Tetrahedron 50 (1994) 10893
15. Åkermark B., Oslob J.D., and Heuschert U. Tetrahedron Lett. 36 (1995) 1325
16. Echavarran A.M., Tamayo N., De Frutos O., and Garcia A. Tetrahedron 50 (1997) 16835
17. Oumar-Mahamat H., Moustrou C., Surzur J.-M., and Berstrand M.P. J. Org. Chem. 54 (1989) 5684
18. Snider B.B., Wan B.Y.F., Buckman B.O., and Foxman B.M. J. Org. Chem. 56 (1991) 5328
19. Citterio A., Sebastiano R., and Carvayal M.C. J. Org. Chem. 56 (1991) 5335
20. Citterio A., Sebastiano R., and Nicolini M. Tetrahedron 49 (1993) 7743
21. Chuang C.-P., and Wang S.-F. Tetrahedron Lett. 35 (1994) 4365
22. Chuang C.-P., and Wang S.-F. J. Chin. Chem. Soc. 44 (1997) 271
23. Chuang C.-P., and Wang S.-F. Tetrahedron 54 (1998) 10043
24. Chuang C.-P., and Wang S.-F. Heterocycles 50 (1999) 489
25. Chuang C.-P., Wu Y.-L., and Jiang M.-C. Tetrahedron 55 (1999) 11229
26. Jiang M.-C., and Chuang C.-P. J. Org. Chem. 65 (2000) 5409
27. Wu Y.-L., Chuang C.-P., and Lin P.-Y. Tetrahedron 57 (2001) 5543
28. Tsai A.-I., Wu Y.-L., and Chuang C.-P. Tetrahedron 57 (2001) 7829
29. Chuang C.-P., and Wu Y.-L. Tetrahedron Lett. 42 (2001) 1719
30. Tseng C.-C., Wu Y.-L., and Chuang C.-P. Tetrahedron 58 (2002) 7625
31. Tseng C.-M., Wu Y.-L., and Chuang C.-P. Tetrahedron 60 (2004) 12249
32. Chen H.-L., Lin C.-Y., Cheng Y.-C., Tsai A.-I., and Chuang C.-P. Synthesis (2005) 977
33. Lin C.-Y., Cheng Y.-C., Tsai A.-I., and Chuang C.-P. Org. Biomol. Chem. (2006) 1097
34. Liao Y.-J., Wu Y.-L., and Chuang C.-P. Tetrahedron 59 (2003) 3511
35. Chuang C.-P., and Wu Y.-L. Tetrahedron 60 (2004) 1841
36. Tsai A.-I., Lin C.-H., and Chuang C.-P. Heterocycles 65 (2005) 2381
37. Tsai A.-I., and Chuang C.-P. Tetrahedron 62 (2006) 2235
38. Jacobsen N., and Torsell K. Acta Chem. Scand. 27 (1973) 3211
39. Brown P.M., and Thomson R.H. J. Chem. Soc., Perkin Trans. 1 (1976) 997
40. Citterio A., Arnoldi A., and Minisci F. J. Org. Chem. 44 (1979) 2674
41. Citterio A., Vismara E., and Bernardi R. J. Chem. Res., Synop. (1983) 88
42. Citterio A., Vismara E., and Bernardi R. J. Chem. Res., Miniprint (1983) 876
43. Williams D.R., and Clark M.P. Tetrahedron Lett. 39 (1998) 7629
44. Reaction of 1a with β-dicarbonyl compounds produced indole-4,7-diones and indole-2,4,7-triones.
45. Similar 1,2-carbonyl group migration has been reported. See: Ref. 6i.
46. Snider B.B., Merritt J.E., Dombroski M.A., and Buckman B.O. J. Org. Chem. 56 (1991) 5544
47. Snider B.B., and McCarthy B.A. J. Org. Chem. 58 (1993) 6217
48. Ishibashi H., Toyao A., and Takeda Y. Synlett (1999) 1468 Also see: Ref. 6k
49. -3. Crystallographic data for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 646869. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
50. -3. Crystallographic data for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 646872. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
51. Kallmeyer H.-J., and Tappe C. Arch. Pharmacol. 319 (1986) 421
52. Kallmeyer H.-J., and Tappe C. Arch. Pharmacol. 41 (1986) 29