'On water': unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension

Tetrahedron Letters

Volumn 50, Issue 43, 2009, Pages 5896-5902

  Tandon, Vishnu K ^a   Maurya, Hardesh K ^a  

^a UNIVERSITY OF LUCKNOW   (India)

Author keywords

Amines; Amino acids; Green synthesis; Naphthoquinones; Quinone; Thiols; Water

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALIPHATIC AMINE; AMINE; AMINO ACID; AROMATIC AMINE; HETEROCYCLIC AMINE; HYDRAZINE DERIVATIVE; QUINONE DERIVATIVE; SOLVENT; SULFIDE; THIOESTER; THIOL DERIVATIVE; WATER;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 69749108403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.149     Document Type: Article

References (55)

1. Herrerias C.I., Xiaoquan Y., Li Z., and Li C.-J. Chem. Rev. 107 (2007) 2546
2. Feng C.-G., Wang Z.-Q., Shao C., Xu M.-H., and Lin G.-Q. Org. Lett. 10 (2008) 4101
3. Yang J., and Breslow R. Angew. Chem., Int. Ed. 39 (2000) 2692
4. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed. 44 (2005) 3275
5. Dambacher J., Zhao W., El-Batta A., Anness R., Jiang C., and Bergdahl M. Tetrahedron Lett. 46 (2005) 4473
6. Hamada T., Manabe K., and Kobayashi S. J. Am. Chem. Soc. 126 (2004) 7768
7. Yanai H., Saito A., and Taguchi T. Tetrahedron 61 (2005) 7087
8. Moore W.H. Chem. Soc. Rev. 2 (1973) 415
9. Sartori M.F. Chem. Rev. 63 (1963) 279
10. Shishkina R.P., Berezhnaya V.N., and Russ V.N. Chem. Rev. 63 (1994) 139
11. Aguilar-Martinez M., Macias-Ruvalcaba N.A., Bautista-Martinez J.A., Gomez M., Gonzalez F.J., and Gonzalez I. Curr. Org. Chem. 8 (2004) 1721
12. Giorgi-Renault S., Renault J., Gebel-Servaltes P., Baron M., Paolett C., Cros S., Bissery M.C., Lavelte F., and Atassi G. J. Med. Chem. 34 (1991) 38
13. Lin T.S., Xu S.P., Zhu L.Y., Cosby L.A., and Sartorell A.C. J. Med. Chem. 32 (1989) 1467
14. Salman-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M.A., Landry V., Sergheraert C., Croft S.L., Krauth-Siegel R.L., and David-Charvet E. J. Med. Chem. 44 (2001) 548
15. dos Santos E.V.M., Carneiro J.W.d.M., and Ferrira V.F. Bioorg. Med. Chem. 12 (2004) 87
16. Lien J.-C., Huang L.-J., Wang J.-P., Teng C.-M., Lee K.-H., and Kuo S.-C. Bioorg. Med. Chem. 5 (1997) 2111
17. Johnson M.G., Kiyokawa H., Tani S., Koyama J., Morris-Natschke S.L., Mauger A., Bowers-Daines M.M., Langer B.C., and Lee K.-H. Bioorg. Med. Chem. 5 (1997) 1469
18. Miguel del Corral J.M., Castro M.A., Gordaliza M., Martin M.L., Gamito A.M., Cuevas C., and Feliciano A.S. Bioorg. Med. Chem. 14 (2006) 2816
19. Takagi K., Matsuoka M., Hamano K., and Kitao T. Dyes Pigments 5 (1984) 241
20. Matsuoka M., Takagi K., Obasyashi H., Wakasugi K., and Kitao T. J. Soc. Dyers Colour 99 (1983) 257
21. Kikuchi M., Komatsu K., and Nakano M. Dyes Pigments 52 (1990) 107
22. Escolastico C., Santa Maria M.D., Claramunt R.M., Jimeno M.L., Alkorta I., Foces-Foces C., Cano F.H., and Elguero J. Tetrahedron 50 (1994) 12489
23. Catalan J., Febero F., Guijarro M.S., Claramunt R.M., Santa Maria M.D., Foces-Foces M., Cano F.H., Elguero J., and Sastre R. J. Am. Chem. Soc. 112 (1990) 747
24. Tandon V.K., Chhor R.B., Singh R.V., Rai S., and Yadav D.B. Bioorg. Med. Chem. Lett. 14 (2004) 1079-1083
25. Tandon V.K., Singh R.V., and Yadav D.B. Bioorg. Med. Chem. Lett. 14 (2004) 2901
26. Tandon V.K., Yadav D.B., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 3288
27. Tandon V.K., Yadav D.B., Singh R.V., Vaish M., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 3463
28. Tandon V.K., Yadav D.B., Singh R.V., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 5324
29. Tandon V.K., Maurya H.K., Yadav D.B., Tripathi A., Kumar B.M., and Shukla P.K. Bioorg. Med. Chem. Lett. 16 (2006) 5883
30. Tandon V.K., Yadave D.B., Maurya H.K., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. 14 (2006) 6120
31. Tandon V.K., Maurya H.K., Tripathi A., Shiva Keshva B., Shukla P.K., Srivastava P., and Panda D. Eur. J. Med. Chem. 44 (2009) 1086
32. Tandon V.K., and Maurya H.K. Heterocycles 76 (2008) 1007
33. Illos R.A., Harlev E., and Bittner S. Tetrahedron Lett. 46 (2005) 8427
34. Sutovsky Y., Likhtenshtein G.I., and Bittner S. Tetrahedron 59 (2003) 2939
35. Anzenbacher P., Palacios M.A., Jursikova K., and Marquez M. Org. Lett. 7 (2005) 5027
36. Blackburn C. Tetrahedron Lett. 46 (2005) 1405
37. Katritzky A.R., Fedoseyenko D., Mohapatra P.P., and Steel P.J. Synthesis 5 (2008) 0777 and references cited therein
38. Knapp V., and Schmidt S. Ann. 210 (1881) 189
39. Plogemann A. Ber. 15 (1883) 48
40. Yerushalmi S., Lemcoff G., and Bittner S. Synthesis 2 (2007) 239
41. Orden, M.; Teresa, M.; Sun, H.; Chamudis, S. T.; Moya, A. C.; Rodriguez, F. B.; Ocana, M.; Victoria, M. PCT Int. Appl., 2007, WO 2007026041.
42. Kallmayer H.-J., and Thierfelder B. Pharmazie 58 (2003) 104
43. Huang S.-T., Kuo H.-S., Hsiao C.-L., and Lin Y.-L. Bioorg. Med. Chem. 10 (2002) 1947
44. Brun M.-P., Braud E., Angotti D., Mondésert O., Quaranta M., Montes M., Miteva M., Gresh N., Ducommun B., and Garbay C. Bioorg. Med. Chem. 13 (2005) 4871
45. Padia, J. K.; O'Brien, S.; Lu, J. Pikul, S. PCT Int. Appl., 2005, 77, WO 2005013903.
46. Aly A.A., Hassan A.A., Mohamrd N.K., and Mourad A.-F.F. Pharmazie 52 (1997) 282
47. Wang X.-L., Zheng X.-F., and Reiner J. Synlett 6 (2006) 942
48. Sarhana E.-W.A.O., El-Dean A.M.K., and Abdel-Monem M.I. Monatshefte fuer Chemie 129 (1998) 205
49. Bhattacharya S. Molecules 5 (2000) M160
50. Wang X.L., Zheng X.F., Wang L., Reiner J., Xie W.L., and Chang J.B. Synthesis 7 (2007) 0989
51. Dallinger D., and Kappe C.O. Chem. Rev. 107 (2007) 2563
52. Representative procedure for the synthesis: Suspension of quinone 1 (0.5 mmol) in water (3 mL) and amines, hydrazines, amino acids, or thiols (solid, 0.5 mmol or liquid, 0.6 mmol) 2 was smoothly stirred at room temp. or 50 °C for 10 min to 12 h. and workup as shown in Table 3 and Table 5. Column chromatography (if required) of the reaction mixture (hexane/EtOAc 50:1→15:1) gave 3 as orange or red solid.
53. Döpp D., Gomaa M.A.-M., Henkel G., and El-Din A.M.N. J. Heterocycl. Chem. 32 (1995) 603
54. Nagami T., Yoshihara K., and Nagakura S. Bull. Chem. Soc. Jpn. 45 (1972) 122
55. Dwivedi P.C., and Agarwal R. Indian J. Chem. 24A (1985) 100