Reaction between anthranilic acids, salicylaldehydes and isocyanides in water: an efficient synthesis of 2-{[2-(alkylimino)-1-benzofuran-3-yliden]amino}benzoic acids

Tetrahedron Letters

Volumn 51, Issue 1, 2010, Pages 27-29

  Adib, Mehdi ^a   Mahdavi, Mohammad ^a   Bagherzadeh, Sharareh ^a   Zhu, Long Guan ^b   Rahimi Nasrabadi, Mehdi ^c  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ZHEJIANG UNIVERSITY   (China)

^c IMAM HOSSEIN UNIVERSITY   (Iran)

Author keywords

Anthranilic acids; Isocyanides; Multicomponent reactions; Salicylaldehydes; Synthesis in water

Indexed keywords

ANTHRANILIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; CYANIDE; SALICYLALDEHYDE; WATER;

ARTICLE; HEATING; ONE POT SYNTHESIS;

EID: 70649105563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.017     Document Type: Article

References (32)

1. Bagley M.C., Dale J.W., and Bower J. Chem. Commun. (2002) 1682-1683
2. Mont N., Teixidó J., Borrell J.I., and Kappe C.O. Tetrahedron Lett. 44 (2003) 5385-5387
3. Simon C., Constantieux T., and Rodriguez J. Eur. J. Org. Chem. 24 (2004) 4957-4980
4. Cui S.L., Lin X.F., and Wang Y.G. J. Org. Chem. 70 (2005) 2866-2869
5. Huang Y.J., Yang F.Y., and Zhu C.J. J. Am. Chem. Soc. 127 (2005) 16386-16387
6. Ramón D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602-1634
7. Dömling A. Chem. Rev. 106 (2006) 17-89
8. Dömling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
9. Ugi I. Isonitrile Chemistry (1971), Academic Press, London
10. Ugi I. Angew. Chem., Int. Ed. Engl. 21 (1982) 810-819
11. Ugi I., and Steinbrükner C. Angew. Chem. 72 (1960) 267-268
12. Giovenzana G.B., Tron G.C., Di Paola S., Menegotto I.G., and Pirali T. Angew. Chem., Int. Ed. 45 (2006) 1099-1102
13. Ngouansavanh T., and Zhu J.P. Angew. Chem., Int. Ed. 45 (2006) 3495-3497
14. El Kaïm L., Grimaud L., and Oble J. Angew. Chem., Int. Ed. 44 (2005) 7961-7964
15. Hulme C., and Gore V. Curr. Med. Chem. 10 (2003) 51-80
16. Orru R.V.A., and De Greef M. Synthesis (2003) 1471-1499
17. Zhu J.P. Eur. J. Org. Chem. (2003) 1133-1144
18. Janvier P., Sun X.W., Bienaymé H., and Zhu J.P. J. Am. Chem. Soc. 124 (2002) 2560-2567
19. Fayol A., and Zhu J.P. Angew. Chem., Int. Ed. 41 (2002) 3633-3635
20. Li C.-J., and Chan T.H. Organic Reactions in Aqueous Media (1997), Wiley, New York
21. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Thomson Science, Glasgow, Scotland
22. Li C.-J. Chem. Rev. 105 (2005) 3095-3165
23. Breslow R. Acc. Chem. Res. 24 (1991) 159-164
24. Breslow R. Acc. Chem. Res. 37 (2004) 471-478
25. Adib M., Sheibani E., Bijanzadeh H.R., and Zhu L.G. Tetrahedron 64 (2008) 10681-10686
26. Adib M., Sayahi M.H., Mahernia S., and Zhu L.G. Tetrahedron Lett. 49 (2008) 945-947
27. Adib M., Mohammadi B., and Bijanzadeh H.R. Synlett (2008) 3180-3182
28. Adib M., Mohammadi B., and Bijanzadeh H.R. Synlett (2008) 177-180
29. Adib M., Sayahi M.H., Ziyadi H., Bijanzadeh H.R., and Zhu L.G. Tetrahedron 63 (2007) 11135-11140
30. Adib M., Sheibani E., Mostofi M., Ghanbary K., and Bijanzadeh H.R. Tetrahedron 62 (2006) 3435-3438
31. 3), 99.4 (C), 105.2 and 109.7 (2CH), 109.9 (C), 114.1, 116.5 and 123.4 (3CH), 129.5 (C), 132.4 and 135.6 (2CH), 138.2, 144.6, 151.2 and 154.3 (4C), 173.9 (C{double bond, long}O).
32. 2 = 0.163. CCDC 717398 contains the supplementary crystallographic data for the structure reported in this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.