Revisiting the reaction of β-chloroacroleins with 2-aminophenol: a new observation

Tetrahedron

Volumn 64, Issue 3, 2008, Pages 582-589

  Bera, Rabin ^a,b   Dhananjaya, G ^a   Singh, Shambu Nath ^a   Ramu, B ^a   Kiran, Sai Uday ^a   Kumar, P Rajender ^a   Mukkanti, K ^b   Pal, Manojit ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

Chloroacroleins; 2 Aminophenol; Chromenoquinoline; Oxepinoquinoline

Indexed keywords

2 AMINOPHENOL; ACROLEIN DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 36549018663     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.101     Document Type: Article

References (24)

1. In: Gilman A.G., Rall T.W., Nies A.S., and Taylor P. (Eds). The Pharmacological Basis of Therapeutics. 8th ed. (1990), Pergamon, New York, NY 1397-1412 Chapter 58
2. Savouret J.F., Chauchereau A., Misrahi M., Lescop P., Mantel A., Bailly A., and Milgrom E. Hum. Reprod. 9 (1994) 7
3. Edwards J.P., West S.J., Marschke K.B., Mais D.E., Gottardis M.M., and Jones T.K. J. Med. Chem. 41 (1998) 303
4. 8-Hydroxyquinoline is a well known antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action, see:. Albert A., Hampton A., and Selbie F.R. Br. J. Exp. Pathol. 35 (1954) 75
5. Jones, T. K.; Goldman, M. E.; Pooley, C. L. F.; Winn, D. T.; Edwards, J. P.; West, S. J.; Tegley, C. M.; Zhi, L.; Hamann, L. G.; Davis, R. L.; Farmer, L. J. PCT Int. Appl. Pub. No. WO 96/19458, 1996.
6. Pfeiffer V.B. J. Prakt. Chem. 151 (1938) 312
7. Jacquignon P., and Goisy N.P. J. Chem. Soc., Perkin Trans. 1 (1972) 4266
8. Sabitha G., and Reddy B.V.S. Synth. Commun. 29 (1999) 4403
9. Balasubramanian K.K., Bindumadhavan G.V., Nair M., and Venugopalan B. Synthesis (1977) 611
10. Swaminathan K.S., Ganesh R.S., Venkatachalam C.S., and Balasubramanian K.K. Tetrahedron Lett. 24 (1983) 3653
11. Rougeot P.E., Moskowitz H., and Miocque M. Tetrahedron Lett. 24 (1983) 2379
12. Kempter G., Zanker P., and Zurner H. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 300 (1967) 829
13. Pal M., Veeramaneni V.R., Nagabelli M., kalleda S.R., Misra P., Casturi S.R., and Yeleswarapu K.R. Bioorg. Med. Chem. Lett. (2003) 1639
14. Padakanti S., Veeramaneni V.R., Pattabiraman V.R., Pal M., and Yeleswarapu K.R. Tetrahedron Lett. 43 (2002) 8715
15. Swamy N.K., Tatini L.K., Babu J.M., Annamalai P., and Pal M. Chem. Commun. (2007) 1035
16. Venkataraman S., Barange K.D., and Pal M. Tetrahedron Lett. 47 (2006) 7317
17. Chaitanya, K. K.; Pal, M.; Huckaby, A.; Kumar, L. S.; Rajasekhar, B.; Khanna, I.; Pillarisetti, S. R.; Vally, M. K. Abstract no A107, DRL-13156 - an orally active selective cytokine modulator with disease modifying activity in arthritis, Presented at the 14th IRA International Conference, October 15-19, 2006, Cambridge, Maryland, USA.
18. Sekhar B.C., Ramana D.V., and Ramadas S.R. J. Heterocycl. Chem. 38 (2001) 383
19. This process involves isolation of the imino derivative, which was cyclized in refluxing DMF (bp 152.8 °C).
20. 1=0.049 and Rw=0.1185 for 4576 observed reflections. Due to the change in the conformation of the 'chromeno' ring the independent molecules A and B differ, which is indicated by the difference in the torsion angles C14C15C16O1 (-144.6(5)) and C30C31C32O3 (-157.1(4)), respectively. The phenolic OH of A showed an intermolecular hydrogen bonding with the hydroxyl oxygen of B. Crystallographic data (excluding structure factors) for 3e have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 644669.
21. Arnold Z., and Zemlicka J. Collect. Czech. Chem. Commun. 24 (1959) 2385
22. Andrieux J., Battioni J.P., Giraud M., and Molho D. Bull. Soc. Chim. Fr. (1973) 2093
23. 4e While intermediacy of a similar species cannot be ruled out in the present case we, however, failed to detect or isolate a corresponding carbaldehyde intermediate under the condition employed during our synthesis of compound 3. Preparation of this intermediate from 1a for further studies was also not successful.
24. 4d The beta-amino imine, when protonated, would be able to undergo ring-closure and then subsequent aromatization to give compound 3 with regeneration of the 'second' 2-aminophenol molecule. We thank the reviewer for bringing this to our notice.{A figure is presented}