Efficient one-pot synthesis of 4-aroyl-2-pyrones: Nucleophilic addition of active methylene groups to 1,2-diaroylacetylenes

Synthetic Communications

Volumn 41, Issue 18, 2011, Pages 2738-2746

  Shankar, Ravi ^a   Shukla, Harsha ^a   Singh, Uma Sharan ^a   Thakur, Vinay ^a   Hajela, K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,2 diaroylacetylenes; 4 Aroyl 2 pyrones; Michael addition

Indexed keywords

1,2 DIAROYLACETYLENE; 4 AROYL 2 PYRONE; CARBENE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROMETRY; INFRARED SPECTROSCOPY; MICHAEL ADDITION; MOLECULE; NUCLEOPHILICITY; ONE POT SYNTHESIS; ROOM TEMPERATURE;

EID: 79959939052     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.515350     Document Type: Article

References (19)

1. Mchlacken, G. P.; Fairlamb, J. S. 2-Pyrone natural products and mimeties: Isolation, characterization, and biological activity. Nat. Prod. Rep. 2005, 22, 369-385.
2. Barrero, A. F.; Oltra, J. E.; Herrador, M. M.; Sanchez, J. F.; Quilez, J. F.; Rojas, F. J.; Reyes, J. F. Gibepyrones: α-Pyrones from Gibberela fujikuroi. Tetrahedron 1993, 49, 141-150.
3. Marrision, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioactive 4-substituted 6-methyl- 2-pyrones with promising cytotoxicity against A2780 and K562 cell lines. Bioorg. Med. Chem. Lett. 2002, 12, 3509-3513. (Pubitemid 35346477)
4. Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lua, F.; Schmidta, J. P. 2-Pyrone possessing antimicrobial and cytotoxic activity. Bioorg. Med. Chem. Lett. 2004, 12, 4285-4299; (Pubitemid 38891390)
5. Schlingmann, G.; Milne, L.; Carter, G. T. New α-pyrones produced by fungal culture LL-11G219 function as androgen receptor ligands. Tetrahedron 1998, 54, 13013-13022. (Pubitemid 28470688)
6. Dickinson, J. Microbial pyran-2-ones and dihydropyran-2-one. Nat. Prod. Rep. 1993, 10, 71-98.
7. Rao, P. N. P.; Amini, M.; Li, H.; Habeeb, A. G.; Knaus, E. E. Design, synthesis, and biological evalution of 6-substituted-3-(4-methanesulfonyl phenyl)-4-phenyl pyran-2-ones: A novel class of diaryl heterocyclic selective cyclooxygenase-2-inhibitors. J. Med. Chem. 2003, 46, 4872-4882.
8. Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Diels-Alder cycloaddition of 2-pyrones and 2-pyridones. Tetrahedron 1992, 48, 9111-1171.
9. Posner, G. H.; Nelson, T.; Kinter, C.; Johnson, N. Diels-Alder cycloaddition using nucleophilic 3-(p-tolythio)-2-pyrone, regiocontrolled, and sterocontrolled synthesis of unsaturated, bridged, bicyclic lactones. J. Org. Chem. 1992, 57, 4083-4087.
10. Vara Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B.; Ferguson, D.; Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humbelet, C.; Bhat, T. N.; Liu, B.; Guerin, D. A. M.; Baldwin, E. T.; Erickson, J. W.; Sawyer, T. K. Novel series of achiral low molecular weight and potent HIV-I protease inhibitors. J. Am. Chem. Soc. 1994, 116, 6989-6990; (Pubitemid 24257237)
11. De Clerq, E. Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infection. J. Med. Chem. 1995, 38, 2491-2517;
12. Romines, K. R.; Thaisrivongs, S. Analogs of 4-hydroxy pyrone: Potent, not-peptidic HIV protease inhibitors. Drugs Future 1995, 20, 377-382.
13. Yao, T.; Larock, R. C. Synthesis of isocoumarins and α-pyrones via electrophilic cyclization. J. Org. Chem. 2003, 68, 5936-5942; (Pubitemid 36876908)
14. Larock, R. C.; Doty, M. J.; Han, X. Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes. J. Org. Chem. 1999, 64, 8770-8779. (Pubitemid 129599385)
15. Rousset, S.; Aberbri, M.; Thibonnet, J.; Parrain, J. L.; Duchene, A. Regio- and stereoselective preparation of γ-alkylidenebutenolides or α-pyrones using a Stille reaction and palladium-catalysed oxacyclisation sequence. Tetrahedron Lett. 2003, 44, 7633-7636. (Pubitemid 37130234)
16. 3-catalyzed 1,4-addition of 1,2-allenic ketone with diethyl malonate controlled selective synthesis of β,γ-unsaturated enones and α-pyrones. J. Org. Chem. 2003, 68, 8996-9002; (Pubitemid 37419945)
17. 3-catlyzed michael reaction. Lactonisation reaction of 1,2-allenylketone with EWG. Org. Lett. 2002, 4, 505-507.
18. Santiago, B.; Gonzalo, B.; Isabel, F.; Pedro, J. R. Novel 2-pyrone synthesis via Michael addition of mandelic acid enolate to trans-1,2- diaroylethenes. Tetrahedron Lett. 2004, 45, 8583-8586. (Pubitemid 39369919)
19. Rao, P. N. P.; Uddin, M. J.; Knaus, E. E. Design, Synthesis, and Structure-Activity Relationship Studies of 3,4,6-Triphenylpyran-2-ones as Selective Cyclooxygenase-2 Inhibitors. J. Med. Chem. 2004, 47, 3972-3990. (Pubitemid 38970959)