Efficient, solvent-free, microwave-enhanced condensation of 5,5-dimethyl-1,3-cyclohexanedione with aldehydes and imines using LiBr as inexpensive, mild catalyst

Synthetic Communications

Volumn 40, Issue 4, 2010, Pages 510-517

  Kumar, Dhruva ^a   Sandhu, Jagir S ^a  

^a PUNJABI UNIVERSITY   (India)

Author keywords

3 cyclohexanedione; 5 5 dimethyl 1; Aldehydes; Imines; LiBr; Solvent free; Xanthenedions

Indexed keywords

ALDEHYDE; BROMINE DERIVATIVE; CYCLOHEXANE DERIVATIVE; IMINE; LITHIUM DERIVATIVE; XANTHENE DERIVATIVE;

ARTICLE; CATALYST; DRUG SYNTHESIS; MICROWAVE IRRADIATION; POLYMERIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 76149098819     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902987792     Document Type: Article

References (30)

1. (a) Stilo, A.; Visentin, D. S.; Clara, C. A.; Gasco, M.; Ermondi, G.; Gasco, A. New 1,4-dihydropyridines conjugated to furoxanyl moieties, endowed with both nitric oxide-like and calcium channel antagonist vasodilator activities. J. Med. Chem. 1998, 41, 5393;
2. (b) Thull, U.; Testa, B. Screening of unsubstituted cyclic compounds as inhibitors of monoamine oxidases. Biochem. Pharmacol. 1994, 47, 2307;
3. (c) Shanmugam, P.; Ramak, V. T.; Srividya, B. N; Ramamurthy, P.; Gunasekaran, K.; Velmurugan, D. Synthesis and laser properties of 9-alkyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives. J. Chem. Soc, Perkin Trans. 1998, 999;
4. (d) Srividya, N.; Velmurugan, P.; Shanmugam, P.; Ramamurthy, P.; Ramak, V. T. Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes. J. Org. Chem. 1996, 61, 5083;
5. (e) Tu, S.; Miao, C; Gao, Y.; Fang, F.; Zhuang, Q.; Feng, Y.; Shi, D. A Novel cascade reaction of aryl aldoxime with dimedone under microwave irradiation: The synthesis of N-hydroxylacri-dine. Synlett 2004, 255.
6. (a) Rong, L.; Li, X.; Wang, H.; Shi, D.; Tu, S.; Zhuang, Q. Reaction of imines with 5,5-dimethyl-1,3-cyclohexandione. Synth. Commun. 2006, 36, 2345;
7. 3+-montmorillonite as a cost-effective and recyclable solid acidic catalyst for the synthesis of xanthenediones. Catal. Commun. 2007, 8, 673;
8. (b) Jin, T.-S.; Zhang, J.-S.; Wang, A.-Q.; Li, T.-S. Solid-state condensation reaction between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature. Synth. Commun. 2005, 35, 2339;
9. 2O-promoted green preparation of xanthenedione derivatives in ionic liquids. Can. J. Chem. 2005, 83, 16;
10. (c) Fan, X.; Li, Y.; Zhang, X.; Qu, G.; Wang, J. An efficient and green preparation of 9-arylacridine-1,8-dione derivatives. J. Heteroatom Chem. 2007, 18, 786;
11. (d) Horning, E. G.; Horning, M. J. Methone derivatives of aldehydes. J. Org. Chem. 1946,11, 95;
12. Love, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. Hantzsch-type dihydropyr-idine hypotensive agents. J. Med. Chem. 1974,17, 956;
13. Kamalljit, S.; Jasbir, S.; Harjit, S. A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazi-nanes and oxazolidines with carbon nucleophiles. Tetrahedron 1996, 52, 14273;
14. (e) Martin, N.; Quinteiro, M.; Seoane, C. Synthesis and conformational study of acridine derivatives related to 1,4-dihydropyridines. J. Heterocycl. Chem. 1995, 32, 235;
15. (e) Tu, S.; Lu, Z.; Shi, D.; Yao, C.; Gao, Y.; Guo, C. A convenient synthesis of 9-aryl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine- 1,8-diones under microwave irradiation without solvent. Synth. Commun. 2002, 32, 2181;
16. Tu, S.; Zhou, J.; Lu, Z.; Deng, X., Shi, D.; Wang, S. Condensation of aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexanedione without catalyst. Synth. Commun. 2002, 32, 3063;
17. Suarez, M.; Loupy, A.; Salfran, E.; Moran, L.; Rolando, E. Synthesis of decahydroacridines under microwaves using ammonium acetate supported on alumina. Heterocycles 1999, 51, 21;
18. Wang, X.; Shi, D.; Wang, S.; Tu, S. Synthesis of 9-aryl-10-(4- methylphenyl)polyhydroacridine under microwave irradiation. Chin. J. Org. Chem. 2003, 11, 1291;
19. (f) Tu, S.; Yuan, G.; Xiaohong, L.; Sifu, T.; Xiaojian, Q. Microwave-induced reaction of aromatic aldehyde with 5,5-dimethyl-1,3- cyclohexandione in solid or liquid phase. Chin. J. Org. Chem. 2001, 21, 1164;
20. (f) Jin, T. S.; Zhang, J. S.; Xiao, J. C.; Wang, A. Q.; Li, T. S. Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives catalized by p-dodecylbenzenesulfonic acid in aqueous media. Synlett. 2004, 866;
21. (g) Jin, T.-S.; Zhang, J.-S.; Guo, T.-T.; Wang, A.-Q.; Li, T.-S. One-pot clean synthesis of 1,8-dioxo-decahydroacridines catalyzed by p-dodecylbene-zenesulfonic acid in aqueous media. Synthesis 2004, 2001;
22. (g) Jin, T.-S.; Wang, A.-Q.; Ma, H.; Zhang, J.-S.; Li, T.-S. The reaction of aromatic aldehydes and 5,5-dimethyl-1, 3-cyclohexanedione under solvent-free grinding conditions. Indian J. Chem. Sect. B 2006, 45, 470;
23. (a) Daqing, S.; Qiya, Z.; Jing, C.; Xiangshan, W.; Tu, S.; Hongwen, H. Reaction of aromation aldehydes with 5,5-diemthyl-1,3-cyclohexandione in water. Chin. J. Org. Chem. 2003, 23, 694.
24. (a) Laskar, D. D.; Prajapti, D.; Sandhu, J. S. Lithium bromide-catalyzed Ehrlich-Sachs reactions using solvent-free conditions. Synth. Commun. 2001, 31, 1427;
25. (b) Baruah, P. P.; Gadhwal, S.; Prajapati, D.; Sandhu, J. S. The Biginelli condensation: A novel and efficient regioselective synthesis of dihydropyrimidin-2(1H)-ones using lithium bromide. Chem. Lett. 2002, 1038;
26. (c) Saini, A.; Suresh; Sandhu, J. S. LiBr: A mild Lewis acid catalyst for efficient one-pot synthesis of a-amino nitriles. Synth. Commun. 2008, 38, 3655;
27. (d) Saini, A.; Kumar, S.; Sandhu, J. S. A new LiBr-catalyzed, facile, and efficient method for the synthesis of 14-alkyl or aryl-14H dibenzo[a,j] xanthenes and tetra-hydrobenzo[b]pyrans under solvent-free conventional and microwave heating. Synlett. 2006, 1928;
28. (e) Ono, F.; Negoro, R.; Sato, T. Lithium bromide, a novel and highly effective catalyst for monothioa-cetalization of acetals under mild reaction conditions. Synlett. 2001, 1581;
29. (f) Seeback, D.; Thaler, A.; Blaser, D.; Ko, S. Y. Transesterifications with 1,8-diazabicyclo[5.4.0]undec-7-ene-lithium bromide (DBU=LiBr)-Also applicable to cleavage of peptides from resins in Merrifleld syntheses. Helv. Chim. Acta 1991, 74, 1102.
30. Firouzabadi, H.; Karimi, M.; Eslami, S. Lithium trifluoromethanesulfonate (LiOTf) as a highly efficient catalyst for chemoselective dithioacetalization of carbonyl compounds under neutral and solvent-free conditions. Tetrahedron Lett. 1999, 40, 4055.