Convenient, cost-effective, and mild method for the N-acetylation of anilines and secondary amines

Synthetic Communications

Volumn 35, Issue 9, 2005, Pages 1189-1195

  Prasad, H S ^a   Srinivasa, G R ^a   Channe Gowda, D ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

Ammonium acetate; Anilines; N Acetylation; Secondary amines

Indexed keywords

ACETIC ACID; AMINO ACID; AMMONIUM ACETATE; ANILINE;

ACETYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COST EFFECTIVENESS ANALYSIS; TEMPERATURE;

EID: 18744363017     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200054764     Document Type: Article

References (24)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999, 150 pp.
2. Pearson, A. L.; Roush, W. J. Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups; John Wiley and Sons: Chichester, UK, 1999; pp. 9-16.
3. Hofle, G.; Steglich, W.; Vorbruggen, H. 4-Dialkylaminopyridines as highly active acylation catalysts. Angew. Chem., Int. Ed. Engl. 1978, 17, 569-583.
4. Saravanan, P.; Singh, V. K. An efficient method for acylation reactions. Tetrahedron Lett. 1999, 40, 2611-2614.
5. 2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation. Tetrahedron Lett. 2002, 43, 4261-4265.
6. Chauhan, K. K.; Frost, C. G. Advances in indium-catalysed organic synthesis. J. Chem. Soc., Perkin Trans. 1 2000, 3015-3019.
7. Li, A.; Li, T.; Ding, T. Montmorillonite K-10 and KSF as remarkable acetylation catalysts. Chem. Commun. 1997, 1389-1390.
8. De, S. K. Ruthenium (III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines. Tetrahedron Lett. 2004, 45, 2919-2922.
9. Chavan, S. P.; Anand, R.; Pasupathy, K.; Rao, B. S. Catalytic acetylation of alcohols, phenols, thiols and amines with zoelite H-FER under solventless conditions. Green Chemistry 2001, 3, 320-322.
10. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis-A review. Tetrahedron 2001, 57, 9225-9283.
11. Xu, D.; Prasad, K.; Repic, O.; Blacklock, T. J. Ethyl trifluoroacetate: A powerful reagent for differentiating amino groups. Tetrahedron Lett. 1995, 36, 7357-7360.
12. Kisfaludy, L.; Mohacsi, T.; Low, M.; Drexler, F. Pentafluorophenyl acetate: A new, highly selective acetylating agent. J. Org. Chem. 1979, 44, 654-656.
13. Kikugawa, Y.; Mitsui, K.; Sakamoto, T.; Kawase, M.; Tamiya, H. N-methoxydiacetamide: A new selective acetylating agent. Tetrahedron Lett. 1990, 31, 243-246.
14. Kunieda, T.; Higuchi, T.; Abe, Y.; Hirobe, M. Highly selective acylation of amines and alcohols by poly (3-acyl-2-oxazolone). Tetrahedron Lett. 1982, 23, 1159-1160.
15. Kondo, K.; Sekimoto, E.; Nakao, J.; Murakami, Y. Studies on development of sufficiently chemoselective N-acylation reagents: N-acyl-N-(2,3,4,5,6- pentafluorophenyl)methanesulfonamides. Tetrahedron 2000, 56, 5843-5856.
16. Murakami, Y.; Kondo, K.; Miki, K.; Akiyama, Y.; Watanabe, T.; Yokoyama, Y. The ortho-substituted N,N-diacetylaniline as a selective acetylating reagent. Tetrahedron Lett. 1997, 38, 3751-3754.
17. Atkinson, R. S.; Barker, E.; Sutcliffe, M. J. N-acetyl-N-acyl-3- aminoquinazolinones as chemoselective acetylating agents. Chem. Commun. 1996, 1051-1052.
18. Ringold, H. J.; Loken, B.; Rosenkranz, G.; Sondheimer, F. Steroids. LXXIII. The direct Oppenauer oxidation of steroidal formate esters. A new synthesis of 17α-hydroxyprogesterone. J. Am. Chem. Soc. 1956, 78, 816-819.
19. Finan, P. A.; Fothergill, G. A. The preparation of acid amides from acid chlorides. J. Chem. Soc. 1962, 2824-2825.
20. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Lead-catalyzed synthesis of azo compounds by ammonium acetate reduction of aromatic nitro compounds. Synth. Commun. 2003, 33, 4221-4227.
21. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Hydrogenative cleavage of azo compounds catalyzed by commercial zinc dust using ammonium acetate. Indian J. Chem. 2004, 43B, 192-195.
22. Lazar, L.; Martinek, T.; Bernath, G.; Fulop, F. A simple synthesis of β-alkyl-substituted β-amino acids. Synth. Commun. 1998, 28, 219-224.
23. Vogel, A. I. In Text Book of Practical Organic Chemistry; Addition Wesely Longman Limited: UK, 1997, pp. 1363-1365.
24. Vogel, A. I. Text Book of Practical Organic Chemistry; Addition Wesely Longman Limited: UK, 1997; p. 1372.