Perchloric acid-silica (HClO4·SiO2)-catalyzed synthesis of 14-alkyl- or 14-aryl-14H-dibenzo[a,,j]xanthenes and N-[(2-hydroxynaphthalen-1-yl)methyl]amides

Helvetica Chimica Acta

Volumn 90, Issue 7, 2007, Pages 1330-1334

  Das, Biswanath ^a   Kumar, D Nandan ^a   Laxminarayana, Keetha ^a   Ravikanth, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROGENEOUS CATALYSTS; PERCHLORIC ACIDS; REACTANTS;

AMIDES; CATALYSIS; INORGANIC ACIDS; REACTION KINETICS; SILICA; SYNTHESIS (CHEMICAL);

OLEFINS;

14 (3 NITROPHENYL)14H DIBENZO[A,J]XANTHENE; 14 (4 METHOXYPHENYL)14H DIBENZO[A,J]XANTHENE; 14 (4 METHYLPHENYL)14H DIBENZO[A,J]XANTHENE; 14 ISOPROPYL 14H DIBENZO[A,J]XANTHENE; 2 NAPHTHOL; ACETAMIDE; ACRYLAMIDE; ALDEHYDE DERIVATIVE; AMIDE; BENZAMIDE; N [(2 BROMOPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL]UREA; N [(2 HYDROXYNAPHTHALEN 1 YL)(4 HYDROXYPHENYL)METHYL]ACETAMIDE; N [(2 HYDROXYNAPHTHALEN 1 YL)(4 METHYLPHENYL)METHYL]PROP 2 ENAMIDE; N [(2 HYDROXYNAPHTHALEN 1 YL)NAPHTHALEN 1 YLMETHYL]BENZAMIDE; PERCHLORIC ACID; SILICON DIOXIDE; UNCLASSIFIED DRUG; UREA; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34547635607     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790134     Document Type: Article

References (30)

1. J. P. Poupelin, G. Saint-Ruft, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 1978, 13, 67.
2. R. W. Lambert, J. A. Martin, J. H. Merrett, K. E. B. Parkes, G. J. Thomas, PCT Int. Appl. WO 9706178, 1997 (Chem. Abstr. 1997, 126, 212377y).
3. T. Hideo, Jpn. Tokkyo koho JP 56005480, 1981 (Chem. Abstr. 1981, 95, 80922b).
4. R. M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 1998, 45, 833.
5. G. Saint-Ruf, A. De, H. T. Hieu, Bull. Chim. Ther. 1972, 7, 83;
6. G. Saint-Ruf, H. T. Hieu, J. P. Poupelin, Naturwissenschaften 1975, 62, 584.
7. A. Banerjee, A. K. Mukherjee, Stain Technol. 1981, 56, 83;
8. S. M. Menchen, S. C. Benson, J. Y. L. Lam, W. Zhen, D. Sun, B. B. Rosenblum, S. Khan, M. Taing, U.S. Pat. 6,583,168, 2003 (Chem. Abstr. 2003, 139, 54287f).
9. C. G. Knight, T. Stephens, Biochem. J. 1989, 258, 683.
10. O. Sirkecioglu, N. Talinli, A. Akar, J. Chem. Res., Synop. 1995, 502.
11. B. Ravindranath, T. R. Seshadri, Phytochemistry 1973, 12, 2781.
12. P. Papini, R. Cimmarusti, Gazz. Chim. Ital. 1947, 142.
13. R. N. Sen, N. Sarkar, J. Am. Chem. Soc. 1925, 47, 1079.
14. K. Ota, T. Kito, Bull. Chem. Soc. Jpn. 1976, 49, 1167.
15. D. W. Knight, P. B. Little, J. Chem. Soc, Perkin Trans. 1 2001, 14, 1771.
16. A. Bekaert, J. Andrieux, M. Plat, Tetrahedron Lett. 1992, 33, 2805.
17. C. W. Kuo, J.-M. Fang, Synth. Commun. 2001, 31, 877.
18. C. Ramesh, N. Ravindranath, B. Das, J. Org. Chem. 2003, 68, 7101;
19. C. Ramesh, G. Mahender, N. Ravindranath, B. Das, Tetrahedron Lett. 2003, 44, 1465;
20. B. Das, J. Banerjee, N. Ravindranath, Tetrahedron 2004, 60, 8357.
21. P. K. Mandal, A. K. Misra, Lett. Org. Chem. 2006, 3, 848;
22. B. Das, A. Majhi, J. Banerjee, Tetrahedron Lett. 2006, 47, 7619;
23. A. T. Khan, T. Parvin, L. H. Choudhury, Synthesis 2006, 2497;
24. A. K. Misra, P. Tiwari, G. Agnihotri, Synthesis 2005, 260.
25. B. Das, K. Ravinder Reddy, P. Thirupathi, Tetrahedron Lett. 2006, 47, 5855;
26. B. Das, K. Venkateswarlu, M. Krishnaiah, H. Holla, Tetrahedron Lett. 2006, 47, 7551.
27. A. K. Chakrabarti, R. Gulhane, Chem. Commun. 2003, 1896.
28. A. Wolff, V. Boechmer, W. Vogt, F. Ugozzoli, G. D. Andreetti, J. Org. Chem. 1990, 55, 5665;
29. K.-W. No, J. E. Kim, K. M. Kwon, Tetrahedron Lett. 1995, 36, 8453;
30. S. H. Mashraqui, M. B. Patil, H. D. Mistry, S. Ghadigaonkar, A. Meetsma, Chem. Lett. 2004, 33, 1058.