Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles

Tetrahedron Letters

Volumn 51, Issue 29, 2010, Pages 3843-3847

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

^a UNIVERSITY OF LUCKNOW   (India)

Author keywords

2,3 Dichloro 1,4 naphthoquinones; Chloranil; Detergent; Green synthesis; Phenol; Sodium dodecyl sulfate (SDS); Surfactant; Water

Indexed keywords

1,4 NAPHTHOQUINONE; AMINE; CHLORANIL; DETERGENT; DODECYL SULFATE SODIUM; NITROGEN; OXYGEN; SULFUR; THIOL; WATER;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; GREEN CHEMISTRY; MICELLE; REACTION OPTIMIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77954309541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.071     Document Type: Article

References (40)

1. Herrerias, C. I.; Xiaoquan, Y.; Li, Z.; Li, C.-J. Chem. Rev. 2007, 107, 2546.
2. (a)Tandon, V. K.; Maurya, H. K. Tetrahedron Lett. 2009, 50, 5896;
3. (b)Tandon, V. K.; Maurya, H. K.; Verma, M. K.; Kumar, R.; Shukla, P. K. Eur. J. Med. Chem. 2010, 45, 2418.
4. http://en.wikipedia.org/wiki/Surfactant.
5. Gogoi, P.; Hazarika, P.; Konwar, D. J. Org. Chem. 2005, 70, 1934.
6. Xin, B.; Zhang, Y.; Cheng, K. Synthesis 2007, 1970.
7. Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311.
8. Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965.
9. Srivastava, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
10. Shiri, M.; Zolfigol, M. A. Tetrahedron 2009, 65, 587.
11. (a)Moore, W. H. Chem. Soc. Rev. 1973, 2, 415;
12. (b)Sartori, M. F. Chem. Rev. 1963, 63, 279;
13. (c)Shishkina, R. P.; Berezhnaya, V. N.; Russ, V. N. Chem. Rev. 1994, 63, 139;
14. (d)Aguilar-Martinez, M.; Macias-Ruvalcaba, N. A.; Bautista-Martinez, J. A.; Gomez, M.; Gonzalez, F. J.; Gonzalez, I. Curr. Org. Chem. 2004, 8, 1721
15. Tandon, V. K.; Chhor, R. B.; Singh, R. V.; Rai, S.; Yadav, D. B. Bioorg. Med. Chem. Lett. 2004, 14, 1079-1083
16. Tandon, V. K.; Singh, R. V.; Yadav, D. B. Bioorg. Med. Chem. Lett. 2004, 14, 2901
17. Tandon, V. K.; Yadav, D. B.; Chaturvedi, A. K.; Shukla, P. K. Bioorg. Med. Chem. Lett. 2005, 15, 3288
18. Tandon, V. K.; Yadav, D. B.; Singh, R. V.; Vaish, M.; Chaturvedi, A. K.; Shukla, P. K. Bioorg. Med. Chem. Lett. 2005, 15, 3463
19. Tandon, V. K.; Yadav, D. B.; Singh, R. V.; Chaturvedi, A. K.; Shukla, P. K. Bioorg. Med. Chem. Lett. 2005, 15, 5324
20. Tandon, V. K.; Maurya, H. K.; Yadav, D. B.; Tripathi, A.; Kumar, B. M.; Shukla, P. K. Bioorg. Med. Chem. Lett. 2006, 16, 5883
21. Tandon, V. K.; Yadav, D. B.; Maurya, H. K.; Chaturvedi, A. K.; Shukla, P. K. Bioorg. Med. Chem. 2006, 14, 6120
22. (a)Tandon, V. K.; Maurya, H. K.; Tripathi, A.; Shiva Keshva, B.; Shukla, P. K.; Srivastava, P.; Panda, D. Eur. J. Med. Chem. 2009, 44, 1086;
23. (b)Tandon, V. K.; Maurya, H. K.; Mishra, N. N.; Shukla, P. K. Eur. J. Med. Chem. 2009, 44, 3130.
24. Tandon, V. K.; Maurya, H. K. Heterocycles 2008, 76, 1007.
25. Tandon, V. K.; Maurya, H. K. Heterocycles 2009, 77, 611.
26. Valderrama, J. A.; Gonzalez, M. F.; Torres, C. Heterocycles 2003, 60, 2343.
27. Sarhan, A. E.-W. A. O.; El-Dean, A. M. K.; Abdel-Monem, M. I. Monatshefte fuer Chemie 1998, 129, 205.
28. Shvartsberg, M. S.; Ivanchikova, I. D.; Lebedeva, N. I. Tetrahedron Lett. 2000, 41, 5757.
29. Lien, J.-C.; Huang, L.-J.; Teng, C.-M.; Wang, J.-P.; Kuo, S.-C. Chem. Pharm. Bull. 2002, 50, 672.
30. Czekanski, T.; Hanack, M. J. Org. Chem. 1991, 56, 1569.
31. Ishikawa, S.; Hinoshita, H.; Tagaki, M.; Ueno, K. Nippon Kagaku Kaishi 1988, 5, 743
32. Valderrama, J. A.; Leiva, H.; Rodriguez, J. A.; Theoduloz, C.; Schmeda-Hirshmann, G. Bioorg. Med. Chem. 2008, 16, 3687.
33. Musso, H. Angew. Chem., Int. Ed. Engl. 1963, 2, 723.
34. Mueller, P.; Venakis, T.; Eugster, C. H. Helv. Chim. Acta 1979, 62, 2350;
35. Knoevenagel, E.; Bueckel, C. Ber. Dtsch. Chem. Ges. 1901, 34, 3993.
36. Laundry detergent (LD, washing powder) used as surfactant is Ariel, detergent product made in India by Proctor and Gamble home products Ltd, Mumbai 400 099 (Tel.: +91 22 24942113, e-mail: intouch.lm@pg.com) No.:4902430214933, MRP: rupees 2.00, packed 03/2009, net weight: 14 g. while the cost of SDS is Rs. 1123.00 for 25 g in the catalog of sigma-Aldrich (436143-25G)-2008. In place of Ariel, other laundry detergent (washing powder) can also used.
37. Miguel del Corral, J. M.; Castro, M. A.; Gordaliza, M.; Mart́in, M. L.; Gamito, A. M.; Cuevas, C.; Feliciano, A. S. Bioorg. Med. Chem. 2006, 14, 2816
38. Representative procedure for synthesis: phenol (2) (1 mmol) was added to 5 mL aqueous suspension of surfactant (0.5 mol % LD or SDS). After stirring for 5 min, quinone 1 (1 mmol) was added and stirred at room temperature or at temperatures as shown in Tables 2-6. Work-up as shown in the footnote of Tables 1-6 followed by column chromatography (if required) of the reaction mixture (hexane/EtOAc 50:1?0:100) yielded products 3-6 and 8.
39. Eyong,K.O.; Folefoc,G.N.; Kuete, V.; Beng,V.P.; Krohn, K.;Hussain, H.; Nkengfack, A. E.; Saeftel, M.; Sarite, S. R.; Hoerauf, A. Phytochemistry 2006, 67, 605.
40. Lee, D.-M.; Ko, J. H.; Lee, K. I. Monatshefte für Chemie 2007, 138, 741.