Facile method for the monomethylation of anilines

Synthetic Communications

Volumn 27, Issue 9, 1997, Pages 1543-1546

  Ha, Hyun Joon ^a   Ahn, Young Gil ^a  

^a Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; METHYLATION; REACTION ANALYSIS;

EID: 0031011101     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006091     Document Type: Article

References (16)

1. This paper is part 6 in the series of "Lewis acid induced N-methyleneamine equivalents". For part 5 see, Ha, H.-J.; Kang, K.-H.; Suh, J.-M.; Ahn, Y.-G. Tetrahedron Lett. 1996, 37, 7069.
2. For comprehensive reviews see, (a) Tramontini, M.; Angiolini, L. Tetrahedron, 1990, 46, 1791; (b) E. F. Kleinman "Comprehensive Organic Synthesis" ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, pp 893-973.
3. For comprehensive reviews see, (a) Tramontini, M.; Angiolini, L. Tetrahedron, 1990, 46, 1791; (b) E. F. Kleinman "Comprehensive Organic Synthesis" ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, pp 893-973.
4. (a) Ha, H.-J.; Nam, G.-S.; Park, K. P. Tetrahedron Lett. 1990, 31, 1567.
5. (b) Ha, H.-J.; Nam, G.-S.; Park, K. P. Bull. Kor. Chem. Soc. 1990, 11, 485. 9.
6. (c) Ha, H.-J.; Nam, G.-S.; Park, K. P. Synth. Commun. 1991, 21, 155.
7. (d) H.-J.; Ahn, Y.-G. Synth. Commun. 1995, 25, 969.
8. (e) Ha, H.-J.; Ahn, Y.-G.; Chon, J.-K. J. Chem. Soc. Perkin Trans. I 1995, 2631.
9. (f) Ha, H.-J.; Kang, K.-H.; Ahn, Y.-G.; Oh, S.-J. Heterocycles submitted.
10. For recent developments of monomethylation see, (a) Barluenga, J.; Bayon, A. M.; Asensio, G. J. Chem. Soc. Chem. Commun. 1984, 1334. (b) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. I 1990, 767. (c) Akabori, S.; Takanohashi, Y J. Chem. Soc. Perkin Trans. I 1991, 479. (d) Saladino, R.; Crestini, C.; Nicoletti, R. Heterocycles, 1994, 38, 567.
11. For recent developments of monomethylation see, (a) Barluenga, J.; Bayon, A. M.; Asensio, G. J. Chem. Soc. Chem. Commun. 1984, 1334. (b) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. I 1990, 767. (c) Akabori, S.; Takanohashi, Y J. Chem. Soc. Perkin Trans. I 1991, 479. (d) Saladino, R.; Crestini, C.; Nicoletti, R. Heterocycles, 1994, 38, 567.
12. For recent developments of monomethylation see, (a) Barluenga, J.; Bayon, A. M.; Asensio, G. J. Chem. Soc. Chem. Commun. 1984, 1334. (b) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. I 1990, 767. (c) Akabori, S.; Takanohashi, Y J. Chem. Soc. Perkin Trans. I 1991, 479. (d) Saladino, R.; Crestini, C.; Nicoletti, R. Heterocycles, 1994, 38, 567.
13. For recent developments of monomethylation see, (a) Barluenga, J.; Bayon, A. M.; Asensio, G. J. Chem. Soc. Chem. Commun. 1984, 1334. (b) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. I 1990, 767. (c) Akabori, S.; Takanohashi, Y J. Chem. Soc. Perkin Trans. I 1991, 479. (d) Saladino, R.; Crestini, C.; Nicoletti, R. Heterocycles, 1994, 38, 567.
14. Reductive monomethylation of 1,3,5-trialkylhexahydro-1,3,5-triazine was not successful due to its harsh condition to hydrolyze N-methylaminoborane and relatively lower reaction yield.
15. 2 gave similar result in a few cases the procedure with 4 mol equivalents was generally applicable and quite effective in most cases.
16. The large scale reaction with 50 mmol of 1,3,5-triphenylhexahydro-1,3,5-triazine was also quite successful in 91% yield.