Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10

Canadian Journal of Chemistry

Volumn 83, Issue 2, 2005, Pages 110-114

  Mohammadpoor Baltork, Iraj ^a   Abdollahi Alibeik, Mohammad ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

2 imidazolines; Dehydrogenation; Imidazoles; Montmorillonite K 10; Potassium permanganate

Indexed keywords

COMPLEXATION; DEHYDROGENATION; OXIDATION; POTASSIUM COMPOUNDS;

2-IMIDAZOLINES; BIS-IMIDAZOLINES; MONTMORILLONITE K-10; POTASSIUM PERMANGANATE;

NITROGEN COMPOUNDS;

2 IMIDAZOLINE DERIVATIVE; ALKYL GROUP; MONTMORILLONITE; MONTMORILLONITE K 10; PERMANGANATE POTASSIUM; UNCLASSIFIED DRUG;

ARTICLE; DEHYDROGENATION; DRUG STRUCTURE; MELTING POINT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

EID: 19044375201     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v04-171     Document Type: Article

References (25)

1. (a) M.R. Grimmett. Comprehensive heterocyclic chemistry. Vol. 4. Edited by K.T. Potts. Pergamon Press, Oxford. 1984. p. 345;
2. (b) J.G. Lambardino and E.H. Wiseman. J. Med. Chem. 17, 1182 (1974);
3. (c) H.G. Kim, J.K. Lee, J.T. Lee, and C.S. Lee. Bull. Korean Chem. Soc. 21, 345 (2000).
4. A.Y. Usyatinsky and Y.L. Khmelnitsky. Tetrahedron Lett. 41, 5031 (2000).
5. S. Balalaie, M.M. Hashemi, and M. Akhbari. Tetrahedron Lett. 44, 1709 (2003), and refs. cited therein.
6. C.M. Coleman, J.M.D. MacElroy, J.F. Gallagher, and D.F. O'Shea. J. Comb. Chem. 4, 87 (2002).
7. T. Dockner and A. Frank. Ger. Offen. 2 729 017 (1979).
8. L.P. Kyrudes, F.B. Zienty, G.W. Steahly, and H.L. Morrill. J. Org. Chem. 577 (1947).
9. R.E. Klem, H.F. Skinner, H. Walba, and R.W. Isensee. J. Heterocycl. Chem. 403 (1970).
10. Y. Amemiya, D.D. Miller, and FL. Hsu. Synth. Commun. 20, 2483 (1990).
11. P.K. Martin, H.R. Matthews, H. Rapoport, and G. Thyagarajan. J. Org. Chem. 3758 (1968).
12. J.L. Hughey IV, S. Knapp, and H. Schugar. Synthesis, 489 (1980).
13. M. Anastassiadou, G. Baziard-Mouysset, and M. Payard. Synthesis, 1814 (2000).
14. M.E. Campos, R. Jimenez, F. Martinez, and H. Salgado. Heterocycles, 40, 841 (1995).
15. (a) D.G. Lee. Encyclopedia of reagents for organic synthesis. Edited by L.A. Paquette. Wiley, New York. 1995. p. 4274;
16. (b) A. Shaabani, A. Bazgir, F. Teimouri, and D.G. Lee. Tetrahedron Lett. 43, 5165 (2002);
17. (c) I. Mohammadpoor-Baltork, M.M. Khodaei, A.R. Hajipour, and E. Aslani. Monatsh. Chem. 134, 539 (2003).
18. H.O. House. Modern synthetic reactions. 2nd ed. W.A. Benjamin, Inc., Menlo Park, Calif. 1972. p. 274.
19. I. Mohammadpoor-Baltork and M. Abdollahi-Alibeik. Bull. Korean Chem. Soc. 24, 1354 (2003).
20. J.J. Baldwin, P.K. Lumma, F.C. Novello, G.S. Ponticello, and J.M. Sprague. J. Med. Chem. 20, 1189 (1977).
21. R.D. Miller, V.Y. Lee, and C.R. Moylan. Chem. Mater. 6, 1023 (1994).
22. N. Sawa. Nippon Kagaku Zasshi, 89, 868 (1968).
23. W.E. Erner. US Patent 2 847 417 (1958); Chem. Abstr. 53, 4305 (1959).
24. H. Schubert and S. Hofmann. J. Prakt. Chem. (Leipzig), 7, 119 (1958).
25. Y. Kikugawa. Synthesis, 124 (1981).