Clean and atom-economic synthesis of octahydroacridines: Application to essential oil of citronella

Tetrahedron Letters

Volumn 44, Issue 36, 2003, Pages 6809-6812

  Jacob, Raquel G ^a   Perin, Gelson ^a   Botteselle, Giancarlo V ^a   Lenardão, Eder J ^b  

^a UNIVERSIDADE REGIONAL DO NOROESTE DO ESTADO DO RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

Microwave irradiation; Octahydroacridine derivatives; Solvent free reaction

Indexed keywords

ACRIDINE DERIVATIVE; AROMATIC AMINE; CITRONELLAL; ESSENTIAL OIL; OCTAHYDROACRIDINE; SILICON DIOXIDE; SOLVENT; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; SOLID;

BETULACEAE; CITRONELLA;

EID: 0042159884     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01749-0     Document Type: Article

References (33)

1. Weinreb S.M. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 5:1991;401-449 Pergamon, Oxford
2. Borger, D. L.; Weinreb, S. M. Hetero-Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; Chapters 2 and 9.
3. Povarov L.S. Russ. Chem. Rev. 36:1967;656.
4. Linkert F., Laschat S., Knickmeier M. Liebigs Ann. 1995;985.
5. Linkert F., Laschat S., Kotila S., Fox T. Tetrahedron. 52:1996;955.
6. Kiselyov A.S., Smith L. II, Armstrong R.W. Tetrahedron. 1998;5089.
7. Sabitha G., Reddy E.V., Yadav J.S. Synthesis. 2001;1979.
8. Yadav J.S., Reddy S., Rao C.V., Srinivas R. Synlett. 2002;993.
9. Laschat S., Lauterwein J. J. Org. Chem. 58:1993;2856.
10. Laschat S., Noe R., Riedel M., Krüger C. Organometallics. 12:1993;3738.
11. Temme O., Laschat S. J. Chem. Soc., Perkin Trans. 1. 1995;125.
12. Schulte J.L., Laschat S., Kotila S., Hecht J., Fröhlich R., Wibbeling B. Heterocycles. 43:1996;2713.
13. Sabitha G., Reddy E.V., Yadav J.S. Synthesis. 2002;409.
14. Ermolaeva, V. G.; Yashunskii, V. G.; Polezhaeva, A. I.; Mashkovskii, M. D. Khim. Farm. Zh. 1968, 2, 20; Chem. Abstr. 1968, 69, 106517p Canas-Rodriguez, A.; Canas, R. G.; Mateo-Bernardo, A. An. Quim., Ser. C. 1987, 83, 24; Chem. Abstr. 1988, 108, 112191t.
15. Lafargue P., Moriniere J.L., Pont P., Mennier J.C.R. Acad. Sci., Ser. C. 270:1970;1186.
16. Schültz H., Ebel S., Fitz H. Arzneim. Forsch. 35:1985;1015.
17. Layer R.W., Westfahl J.C. J. Org. Chem. 44:1979;1146.
18. Sakane S., Matsumura Y., Yamamura Y., Ishida Y., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 105:1983;672.
19. Sakanishi K., Mochida I., Okazaki H., Soeda M. Chem. Lett. 1990;319. and references cited therein.
20. Sakanishi K., Ohira M., Moshida I. J. Chem. Soc., Perkin Trans. 2. 1988;1769.
21. Nagai M. Bull. Soc. Chem. Jpn. 64:1991;330.
22. Tanaka, J.; Takabe, K.; Taniguchi, K.; Katagiri, T. Nippon Kogaku Kaishi 1981, 1043; Chem. Abstr. 1981, 95, 219818t.
23. Anastas P.T., Warner J. Green Chemistry: Theory and Practice. 1998;Oxford University Press, Oxford.
24. For a review concerning the use of MW and other non-classical energy fonts in organic synthesis, see: Nüchter M., Ondruschka B., Jungnickel A., Müller U. J. Phys. Org. Chem. 13:2000;579.
25. For reviews in MW solvent-free using supported reagents, see: (a) Varma, R. S. Green Chem. 1999, 43; (b) Varma, S. Pure Appl. Chem. 2001, 73, 193.
26. For reviews in MW solvent-free using supported reagents, see: (a) Varma, R. S. Green Chem. 1999, 43; (b) Varma, S. Pure Appl. Chem. 2001, 73, 193.
27. Diaz-Ortiz A., Hoz A., Langa F. Green Chem. 2:2000;165. and references cited therein.
28. Jacob R.G., Perin G., Loi L.N., Pinno C.S., Lenardão E.J. Tetrahedron Lett. 44:2003;3605.
29. 2 (1.0 g) and water (3.0 mL) were added. The suspension was stirred for 15 min. at room temperature, dried at 80°C for 3 h and for additional 15 h at 150°C in an oven and then cooled in a desiccator.
30. 3) δ 142.9, 131.0, 126.4 (2C), 116.6, 113.5, 50.4, 46.9, 43.2, 35.0, 34.7, 30.8, 27.1, 26.6, 24.6, 22.2. Method B: The procedure aforementioned was followed using citronellal and aniline and the solvent less reaction was stirred at 41-45°C for 3-80 min.
31. 3) δ 140.8, 130.4, 127.5, 124.2, 119.8, 116.0, 50.5, 46.8, 43.5, 35.0, 34.7, 30.9, 27.0, 26.8, 24.7, 22.1, 17.3.
32. a Reunião Anual da Sociedade Brasileira de Química, Poços de Caldas, Brazil, 2002.
33. The oven powers were determined according to described by Kingston, H. M. Introduction to Microwave Sample Preparation-Theory and Practice; Jassie, L. B., Ed.; American Chemical Society, DC, 1988.