A facile route to the synthesis of new 2,3-disubstituted benzocoumarins

Synthetic Communications

Volumn 38, Issue 12, 2008, Pages 2054-2060

  El Shaieb, Kamal M ^a   Shaker, Raafat M ^a   Aly, Ashraf A ^a  

^a El Minia University ^*  (Egypt)

Author keywords

deficient acetylenes; 2 hydroxy 1 naphthaldehyde; Benzo f chromenes

Indexed keywords

2 HYDROXY 1 NAPHTHALDEHYDE; 2,3 BENZOCOUMARIN DERIVATIVE; ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 45749112593     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801997850     Document Type: Article

References (18)

1. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993; Chap 1, p. 1.
2. Butterfield, B. J.; Tabby, J. C.; Griffiths, D. V. Reactions of phosphines with acetylenes: Formation and stereochemistry of 1,2-dicyano-2-phosphoniaethanesulphonate betaines. J. Chem. Soc., Perkin Trans. 1 1979, 1189.
3. Nair, V.; Nair, J. S.; Vinod, A. U. Triphenylphosphane-mediated addition of dimethyl acetylenedicarboxylate to 1,2- and 1,4-benzoquinones: synthesis of novel γ-spirolactones. Synthesis 2000, 1713-1718.
4. Yavari, I.; Ramazani, A. Vinyltriphenylphosphonium salt mediated preparation of dialkyl 2H-1-benzopyran-2,3-dicarboxylates: An efficient one-pot synthesis of 2H-chromene derivatives. J. Chem. Res., Syno. 1996, 382-383.
5. El-Shaieb, K. M. Reaction of dimethyl acetylenedicarboxylate with 2-mercaptoperimidine and 2-mercaptobenzimidazole. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 675-681.
6. + channels: Synthesis and photoreactivity. J. Med. Chem. 1998, 41, 4542-4549.
7. (a) Skulnick, H. I.; Johnson, P. D.; Aristoff, P. A.; Morris, J. K.; Lovasz, K. D.; Howe, D. J.; Watenpaugh, K. D.; Janakiraman, M. N.; Anderson, D. A.; Reischer, R. J.; Schwartz, T. M.; Banitt, L. S.; Tomich, P. K.; Lynn, J. C.; Horng, M.-M.; Chong, K. T.; Hinshaw, R. R.; Dolak, L. A.; Seest, E. P.; Schwende, F. J.; Rush, B. D.; Howard, G. M.; Toth, L. N.; Wilkinson, K. R.; Kakuk, T. J.; Johnson, C. W.; Cole, S. L.; Zaya, R. M.; Zipp, G. L.; Possert, P. L; Dalga, R. J.; Zhong, W.-Z.; Williams, M. G.; Romines, K. R. Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyclooctylpyranones. J. Med. Chem. 1997, 40, 1149-1164;
8. (b) Spino, C.; Dodier, M.; Sotheeswaren, S. Anti-HIV coumarins from calophyllum seed oil. Bioorg. Med. Chem. Lett. 1998, 8, 3475-3478.
9. Crow, F. W.; Duholke, W. K.; Farley, K. A.; Hadden, C. E.; Hahn, D. A.; Kaluzny, B. D.; Mallory, C. S.; Martin, G. E.; Smith, R. F.; Thamann, T. J. Ribose-substituted aromatic amides, method for the production and use thereof as medicaments. J. Heterocycl Chem. 1999, 36, 365-372.
10. Barker, W. M.; Hermodson, M. A.; Link, K. P. 4-Hydroxycoumarins: Synthesis of metabolites and some other derivatives of warfarin. J. Med. Chem. 1971, 14, 167-169.
11. Aly, A. A.; El-Shaieb, K. M. Facile synthesis of 3,6-dihydro-4-phenyl-6- [(Z)phenylimino]-1,3,5-thiadiazine-2,2-dicarbonitriles. J. Chem. Res. 2007, 207-209.
12. Aly, A. A.; NourEl-Din, A. M.; Gomaa, M. A.-M.; Brown, A. B.; Fahmi, M. S. Chemistry of 2,3-diphenylcyclopropenone: Unusual reactivity of 2,3-diphenylcyclopropenone towards N-imidoyl-thioureas: Facile synthesis of 3-aryl-2,5,6-triphenylpyrimidin-4(3H)-one (Part III). J. Chem. Res. 2007, 439-441.
13. Aly, A. A. Cycloadditions of N-[2-(4′-[2.2]paracyclophanyl) ethylidene]methylamine N-oxide with 2,3-diphenylcyclopropenones and dibenzoylacetylene: Synthesis of new paracyclophanyl-pyrroles. J. Chem. Res. 2007, 451-454.
14. Aly, A. A.; Ahmed, E. K.; El-Mokadam, K. M. Reactions of aroylthioureas with acetylenic esters and dibenzoyl ethylene; Selectivity towards the formation of new 1,3-thiazines. J. Heterocycl. Chem. 2007, 44, 1431-1438.
15. Shaker, R. M. Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de]-[1,6]naphthylpyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines. Arkivoc 2006, 14, 59-67.
16. Kumar, R. J.; Krupadanam, G. L. D.; Srimannarayana, G. A new approach to the synthesis of 2-methyl-4H-furo[3,2-c][1]benzopyran-4-ones and 2H,5H-pyrano[3,2-c][1]benzopyran-5-ones. Synthesis 1990, 535-538.
17. Zhang, J.-J.; Schuster, G. B. Ylidions: A new reactive intermediate prepared by photosensitized one-electron oxidation of phenacyl sulfonium ylides. J. Am. Chem. Soc. 1989, 111, 7149-7155.
18. Organikum "Organisch Chemisches Grundpraktikum"; VEB Deutscher Verlag der Wissenschaften: Berlin, 1973.