Atom-Economic Synthesis of Functionalized Octahydroacridines from Citronellal or 3-(Phenylthio)-citronellal

Synthetic Communications

Volumn 39, Issue 15, 2009, Pages 2747-2762

  Jacob, Raquel G ^a   Silva, Marcio S ^a   Mendes, Samuel R ^a   Borges, Elton L ^a   Lenardao, Eder J ^a   Perin, Gelson ^a  

^a FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

Citronellal; Octahydroacridines; Solvent free; Supported catalysis

Indexed keywords

2 (PHENYLTHIO)CITRONELLAL; 3 (PHENYLTHIO)OCTAHYDROACRIDINE DERIVATIVE; ACRIDINE DERIVATIVE; AROMATIC AMINE; CITRONELLAL; SILICON DIOXIDE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION ANALYSIS; REACTION TIME;

EID: 67650299461     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802663469     Document Type: Article

References (33)

1. (a) Weinreb, S. M. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming (Eds.); Pergamon: Oxford, 1991; vol. 5;
2. (b) Borger, D. L.; Weinreb, S. M. Hetero-Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987.
3. (a) Linkert, F.; Laschat, S.; Kotila, S.; Fox, T. Evidence for a stepwise mechanism in formal hetero-Diels-Alder reactions of N-arylimines. Tetrahedron1996, 52, 955;
4. 3. Tetrahedron 1998, 54, 5089;
5. (c) Sabitha, G.; Reddy, E. V.; Yadav, J. S. Bismuth(III) chloride-catalyzed intramolecular hetero Diels-Alder reaction: Application to the synthesis of tetrahydrochromano[ 4,3-b]quinoline derivatives. Synthesis 2001, 1979;
6. (d) Yadav, J. S.; Reddy, S.; Rao, C. V.; Srinivas, R. LPDE-catalyzed intramolecular cyclization of arylimines: A facile synthesis of tetrahydrochromanoquinolines. Synlett 2002, 993.
7. (a) Laschat, S.; Lauterwein, J. Intramolecular hetero-Diels-Alder reaction of N-arylimines: Applications to the synthesis of octahydroacridine derivatives. J. Org. Chem. 1993, 58, 2856;
8. 6-arene)chromium complexes and their diastereoselective intramolecular hetero-Diels-Alder reactions. Organometallics 1993, 12, 3738;
9. 6-(octahydroacridine)- chromiumtricarbonyl complexes with non-polar tails via molecular sieves-catalyzed cyclization of N-arylimines and subsequent diastereoselective complexation. Heterocycles1996, 43, 2713;
10. (d) Temme, O.; Laschat, S. Effect of molecular sieves on the formation and acid-catalysed mono- and bis-cyclization of N-arylimines: Easy entry to polycyclic ring systems by a novel cascade reaction. J. Chem. Soc., Perkin Trans. 1 1995, 125;
11. (e) Sabitha, G.; Reddy, E. V.; Yadav, J. S. Bismuth(III) chloride: An efficient catalyst for the one-pot stereoselective synthesis of octahydroacridines. Synthesis 2002, 409;
12. (f) Mayekar, N. V.; Nayak, S. K.; Chattopadhyay, S. Two convenient one-pot strategies for the synthesis of octahydroacridines. Synth. Commun. 2004, 34, 3111;
13. (g) Yadav, J. S.; Reddy, B. V. S.; Chetia, L.; Srinivasulu, G.; Kunwar, A. C. Ionic liquid accelerated intramolecular hetero-Diels-Alder reactions: a protocol for the synthesis of octahydroacridines. Tetrahedron Lett. 2005, 46, 1039;
14. (h) Lenardão, E. J.; Mendes, S. R.; Ferreira, P. C.; Perin, G.; Silveira, C. C.; Jacob, R. G. Selenium- and tellurium-based ionic liquids and their use in the synthesis of octahydroacridines. Tetrahedron Lett. 2006, 47, 7439.
15. (i) Jacob, R. G.; Perin, G.; Botteselle, G. V.; Lenardão, E. J. Clean and atom-economic synthesis of octahydroacridines: Application to essential oil of citronella. Tetrahedron Lett. 2003, 44, 6809.
16. (a) Canas-Rodriguez, A.; Canas, R. G.; Mateo-Bernardo, A. Tricyclic inhibitors of gastric acid secretion, part V: Octahydroacridines. An. Quim., Ser. C.1987, 83, 24; Chem. Abstr. 1988, 108, 112191t;
17. (b) Lafargue, P.; Moriniere, J. L.; Pont, P.; Mennier, J. C. R. Hexahydroacridones prepared by the hydrolysis of cyclohexenyl-1,4- benzodiazepines. Acad. Sci., Ser. C 1970, 270, 1186;
18. (c) Schü ltz, H.; Ebel, S.; Fitz, H. Screening and detection of tetrazepam and its major metabolites. Arzneim. Forsch. 1985, 35, 1015. For antimalarial activity of acridine derivatives, see, for example;
19. (d) Guetzoyan, L.; Ramiandrasoa, F.; Dorizon, H.; Desprez, C.; Bridoux, A.; Rogier, C.; Pradines, B.; Perrée-Fauvet, M. In vitro efficiency of new acridyl derivatives against Plasmodium falciparum. Bioorg. Med. Chem. 2007, 15, 3278.
20. Layer, R. W.; Westfahl, J. C. Isophorone-aniline condensation product. J. Org. Chem. 1979, 44, 1146.
21. Sakane, S.; Matsumura, Y.; Yamamura, Y.; Ishida, Y.; Maruoka, K.; Yamamoto, H. Olefinic cyclizations promoted by Beckmann rearrangement of oxime sulfonate. J. Am. Chem. Soc. 1983, 105, 672.
22. (a) Sakanishi, K.; Mochida, I.; Okazaki, H.; Soeda, M. Selective hydrogenation of 9-aminoacridine over supported noble metal catalysts. Chem. Lett.1990, 319, and references therein;
23. (b) Sakanishi, K.; Ohira, M.; Moshida, I. Kinetics and stereochemistry in the catalytic hydrogenation of acridine. J. Chem. Soc., Perkin Trans. 2 1988, 1769.
24. (a) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Organoselenium and organotellurium compounds: Toxicology and pharmacology. Chem. Rev. 2004, 104, 6255.
25. 3=KF under solvent-free conditions. Tetrahedron Lett. 2008, 49, 1927;
26. (b) Lenardão, E. J.; Lara, R. G.; Silva, M. S.; Jacob, R. G.; Perin, G. Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions. Tetrahedron Lett. 2007, 48, 7668;
27. (c) Lenardão, E. J.; Ferreira, P. C.; Jacob, R. G.; Perin,G.; Leite, F. P. L. Solvent-free conjugated addition of thiols to citral using KF=alumina: Preparation of 3-thioorganylcitronellals, potential antimicrobial agents. Tetrahedron Lett. 2007, 48, 6763;
28. 4: Easy access to vinyl selenides. Tetrahedron Lett. 2007, 48, 8011;
29. (e) Perin, G.; Jacob, R. G.; Dutra, L. G.; Azambuja, F.; Santos, G. F. F.; Lenardão, E. J. Addition of chalcogenolate anions to terminal alkynes using microwave and solvent-free conditions: Easy access to bis-organochalcogen alkenes. Tetrahedron Lett. 2006, 47, 935;
30. (f) Perin, G.; Jacob, R. G.; Botteselle, G. V.;Kublik, E. L.; Lenardão, E. J.; Cella, R.; Santos, P. C. S. Clean and atom-economic synthesis of α-phenylselenoacrylonitiles and a-phenylseleno-a,β- unsaturated esters by Knoevenagel reaction under solvent-free conditions. J. Braz. Chem. Soc. 2005, 16, 857;
31. (g) Perin, G.; Jacob, R. G.; Azambuja, F.; Botteselle, G. V.; Siqueira, G. M.; Freitag, R. A.; Lenardão, E. J. The first synthesis of β-phenylchalcogeno-a,β-unsaturated esters via hydrochalcogenation of acetylenes using microwave and solvent-free conditions. Tetrahedron Lett. 2005, 46, 1679.
32. The oven powers were determined as described by Kingston, H. M., In Introduction to Microwave Sample Preparation-Theory and Practice; L. B. Jassie (Ed.); American Chemical Society: Washington, DC, 1988.
33. Frö hlich, R.; Grehl, M.; Kramm-Glade, S.; Laschat, S. Two octahydroacridines. Acta Cryst. 1994, C50, 1798.