Efficient one-pot synthesis of precursors of some novel aminochromene annulated heterocycles via domino knoevenagel-hetero-diels-alder reaction

Synthetic Communications

Volumn 43, Issue 11, 2013, Pages 1577-1586

  Parmar, Narsidas J ^a   Teraiya, Shashikant B ^a   Barad, Hitesh A ^a   Sharma, Deepak ^b   Gupta, Vivek K ^b  

^a SARDAR PATEL UNIVERSITY   (India)

^b UNIVERSITY OF JAMMU   (India)

Author keywords

1,3 diketone; Aminochromene; Polyheterocycles; TBA HS; Xanthene

Indexed keywords

AMINOCHROMENE; CHROMENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DOMINO KNOEVENAGEL HETERO DIELS ALDER REACTION; KNOEVENAGEL CONDENSATION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 84876271882     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.652755     Document Type: Article

References (31)

1. For selected books and reviews on domino reactions, see (a) Poulin, J.; Christiane, M.; Barriault, L. Pericyclic domino reactions: Concise approaches to natural carbocyclic frameworks. Chem. Soc. Rev. 2009, 38, 3092-3101;
2. (b) Tietze, L. F., Brasche, G., Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006;
3. (c) Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115-136; (Pubitemid 126637714)
4. (d) Ho, T.-L. Tandem Organic Reactions; John Wiley and Sons: New York, 1992.
5. For reviews on domino sequence initiated by Knoevenagel condensations, see (a) Bandyopadhyay, C.; Maiti, S. Substituent-controlled domino-Knoevenagel- hetero Diels-Alder reaction-A one-pot synthesis of polycyclic heterocycles. Tetrahedron 2010, 66, 7625-7632;
6. (b) Zhu, J., Bienayme, H. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005; 121;
7. (c) Tietze, L. F.; Rackelmann, N. Domino reactions in the synthesis of heterocyclic natural products and analogs. Pure Appl. Chem. 2004, 76, 1967-1983;
8. (d) Tietze, L. F.; Modi, A. Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med. Res. Rev. 2000, 20, 304-322; (Pubitemid 30430010)
9. (e) Tietze, L. F.; Kettschau, G.; Gewart, J. A.; Schuffenhauer, A. Hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Curr. Org. Chem. 1998, 2, 19-62. (Pubitemid 28186811)
10. For recent domino reactions triggered by Knoevenagel condensations, see (a) Baruah, B.; Bhuyan, P. J. Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramolecular domino hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium. Tetrahedron 2009, 65, 7099-7104;
11. (b) Lee, Y. R.; Kim, Y. M.; Kim, S. H. Efficient one-pot synthesis of benzopyranobenzopyrans and naphthopyrano-benzopyrans by domino aldol-type reaction = hetero Diels-Alder reaction of resorcinols and napthols. Tetrahedron 2009, 65, 101-108;
12. (c) Balalaie, S.; Ramezanpour, S.; Bararjanian, M. DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three-component condensation reaction at room temperature. Synth. Commun., 2008, 38, 1078-1089; (Pubitemid 351364149)
13. (d) Dawadi, P. B. S.; Lugtenburg, J. Preparation of 5-cyano-4,6-dimethyl- 2Hpyran-2-one and 3-cyano-5-methoxy-4-methyl-5H-furan-2-one via a one-pot, domino-Knoevenagel process. Synth. Commun., 2010, 40, 2539-2546;
14. (e) Sabitha, G.; Fatima, N.; Reddy, E. V.; Yadav, J. S. First examples of proline-catalyzed domino knoevenagel=hetero-Diels-Alder=elimination reactions. Adv. Synth. Catal. 2005, 347, 1353-1355. (Pubitemid 41273273)
15. Becker, R. S. U. S. Patent 3,567,605, 1971.
16. Mann, C.; Melzig, M.; Weignnd, U. U.S. Patent 6967249 B2, 2005.
17. Mannhold, R.; Cruciani, G.; Weber, H. 6-Substituted benzopyrans as potassium channel activators: Synthesis, vasodilator properties, and multivariate analysis. J. Med. Chem. 1999, 42, 981-991. (Pubitemid 29153427)
18. Conti, C.; Desideri, N. New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders. Bioorg. Med. Chem. 2010, 18, 6480-6488.
19. Norman, B. H. U. S. Patent 0064742 A1, 2008.
20. Brown, C. W.; Liu, S.; Benbrook, D. M. Novel heteroarotinoids as potential antagonists of Mycobacterium bovis BCG. J. Med. Chem. 2004, 47, 1008-1017. (Pubitemid 38176804)
21. Ramesh, E.; Raghunathan, R. Microwave-assisted K-10 montmorillonite clay-mediated Knoevenagel hetero-Diels-Alder reactions: A novel protocol for the synthesis of polycyclic pyrano[2,3,4-kl]xanthenes derivatives. Synth. Commun. 2009, 39, 613-625.
22. Ion, R. M. The photodynamic therapy of cancer-A photosensitization or a photocatalytic process. Prog. Catal. 1997, 2, 55-76.
23. Hideu, T. [1]Benzopyrano[2,3-b]xanthene derivatives. Jpn. Tokkyo Koho JP 56005480, June 27, 1979; Chem. Abstr. 1981, 95, 80922b.
24. Lamberk, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. Preparation of pyrimidine nucleosides as thymidine kinase inhibitors and virucides. PCT Int. Appl. WO 9706178, 1997; Chem. Abstr. 1997, 126, P212377y.
25. Poupelin, J. P.; Saint-Rut, G.; Fussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lakroix, R. Action of hemolysin from Pseudomonas aeruginosa on the Ehrich ascites tumor cells. Eur. J. Med. Chem. 1978, 13, 67-71.
26. Parmar, N. J.; Teraiya, S. B.; Patel, R. A. Tetrabutylammonium hydrogen sulfate-mediated domino reaction: Synthesis of novel benzopyran-annulated pyrano[2,3-c]pyrazoles. Tetrahedron Lett. 2011, 52, 2853-2856.
27. Tietze, L. F.; Denzer, H.; Neumann, M. Stereocontrolled formation of annelated cyclopenianes by intramolecular hetero-Diels-Alder reaction: Synthesis of deoxyloganin from citronellal. Angen. Chem., Int. Ed. Engl. 1987, 26, 1295-1297.
28. Shanmungasundaram, M.; Manikandan, S.; Raghunathan, R. High chemoselectivity in microwave-accelerated intramolecular domino Knoevenagel hetero-Diels-Alder reactions-An efficient synthesis of pyrano[3-2c]coumarin frameworks. Tetrahedron 2002, 58, 997-1003. (Pubitemid 34093846)
29. Khoshkholgh, M. J.; Balalaie, S.; Bijanzadeh, H. R. Synthesis of novel annulated uracils via domino Knoevenagel-hetero-Diels-Alder reaction in aqueous media. Tetrahedron Lett. 2008, 49, 6965-6968.
30. Perrin, D. D.; Amarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.
31. Sheldrick, G.M. SHELX97: Programs for crystal structure analysis, release 97-2. University of Göttingen, Germany, 1997.