Direct oxidative conversion of alcohols, amines, aldehydes, and benzyl halides into the corresponding nitriles with trichloroisocyanuric acid in aqueous ammonia

Synthesis

Volumn , Issue 15, 2010, Pages 2631-2635

  Veisi, Hojat ^a  

^a PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

alcohols; aldehydes; alkyl halides; amines; nitriles; trichloroisocyanuric acid

Indexed keywords

ALKYL HALIDES; AQUEOUS AMMONIA; AROMATIC NITRILES; BENZYL HALIDES; BENZYLIC HALIDES; HIGH YIELD; NITRILES; ONE POT; OXIDATIVE CONVERSION; PRIMARY AMINES; TRICHLOROISOCYANURIC ACID;

ACIDS; ALDEHYDES; ALKYLATION; AMINES; AMMONIA; HYDROCARBONS;

CYANIDES;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMINE; AMMONIA; AROMATIC COMPOUND; HALIDE; NITRILE; OXIDIZING AGENT; SYMCLOSENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; OXIDATION; SYNTHESIS;

EID: 77954940465     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218827     Document Type: Article

References (39)

1. North M, Comprehensive Organic Functional Group Transformations Katritzky A R. Meth-Cohn O Rees C W. Pergamon Oxford 1995
2. Friedrick K, Wallensfels K, The Chemistry of the Cyano Group Rappoport Z Wiley-Interscience New York 1970
3. Fabiani M E., Drug News Perspect. 1999 12 207
4. Comprehensive Organic Transformations Larock R C. VCH Weinheim 1989 976-993
5. Huber V J., Bartsch R A., Tetrahedron 1998 54 9281
6. Nakajima N, Ubukata M, Tetrahedron Lett. 1997 38 2099
7. Bose D S., Jayalakshmi B, J. Org. Chem. 1999 64 1713
8. Kumar H M. S., Reddy B V. S., Reddy P T., Yadav J S., Synthesis 1999 586
9. Bose D S., Narsaiah A V., Tetrahedron Lett. 1998 39 6533
10. Kumar H M. S., Mohanty P K., Kumar M S., Yadav J S., Synth. Commun. 1997 27 1327
11. Kaim L E., Gacon A, Tetrahedron Lett. 1997 38 3391
12. Nakagawa K, Tsuji T, Chem. Pharm. Bull. 1963 11 296
13. Clarke T G., Hampson N A., Lee J B., Morley J R., Scanlon B, Tetrahedron Lett. 1968 9 5685
14. Yamaguchi J, Takeda T, Chem. Lett. 1992 1933
15. Gao S, Herzig D, Wang B, Synthesis 2001 544
16. Yamazaki S, Synth. Commun. 1997 27 3559
17. Moriarty R M., Vaid R K., Duncan M P., Ochiai M, Inenaga M, Nagao Y, Tetrahedron Lett. 1988 29 6913
18. Chen F, Kuang Y, Dai H, Lu L, Huo M, Synthesis 2003 2629
19. Luca L D., Giacomelli G, Synlett 2004 2180
20. Chiampanichayakul S, Pohmakotr M, Reutrakul V, Jaipetch T, Kuhakakarn C, Synthesis 2008 2045
21. Iida S, Togo H, Synlett 2006 2633
22. Iida S, Togo H, Tetrahedron 2007 63 8274
23. Iida S, Togo H, Synlett 2007 407
24. Yamagguchi K, Mizuno N, Angew. Chem. Int. Ed. 2003 42 1480
25. Chen F, Li Y, Xu M, Jia H, Synthesis 2002 1804
26. Mori N, Togo H, Synlett 2005 1456
27. Reddy K R., Maheswari C U., Venkateshwar M, Prashanthi S, Kantam M L., Tetrahedron Lett. 2009 50 2050
28. Iida S, Ohmura R, Togo H, Tetrahedron 2009 65 6257
29. For a recent review on the use of trichloroisocyanuric acid, see:, Tilstam U, Weinmann H, Org. Process Res. Dev. 2002 4 384
30. Ye J, Wang Y, Liu R, Zhang G, Zhang Q, Chen J, Liang X, Chem. Commun. 2003 2714
31. Ye J, Wang Y, Chen J, Liang X, Adv. Synth. Catal. 2004 346
32. Firouzabadi H, Iranpoor N, Hazarkhani H, Synlett 2001 1641
33. Zolfigol M A., Madrakian E, Ghaemi E, Mallakpour S, Synlett 2002 1633
34. Synlett Spotlight 132:, Barros J C., Synlett 2005 2115
35. Ghorbani-Vaghei R, Veisi H, Synthesis 2009 945
36. Ghorbani-Vaghei R, Zolfigol M A., Chegeny M, Veisi H, Tetrahedron Lett. 2006 47 4505
37. Ghorbani-Vaghei R, Shahbazee E, Veisi H, Mendeleev Commun. 2005 207
38. Veisi H, Hemmati S, Veisi H, J. Chin. Chem. Soc. 2009 56 240
39. Ghorbani-Vaghei R, Veisi H, Mol. Divers. 2010 14 249