Selective synthesis of 2-Aryl-2 H - And 4-Aryl-4 H -3,5-diformylpyrans from acetal with aromatic aldehydes catalyzed by lewis acids

Synlett

Volumn , Issue 6, 2011, Pages 857-861

  Horikawa, Norihide ^a   Obora, Yasushi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

acetals; aldehydes; catalysis; Lewis acids; pyrans

Indexed keywords

1,1,3,3 TETRAMETHOXYPROPANE; 2 ARYL 2H 3,5 DIFORMYLPYRAN DERIVATIVE; 2 ARYL 2H DIFORMYLPYRAN DERIVATIVE; 4 ARYL 4H 3,5 DIFORMYLPYRAN DERIVATIVE; 4 ARYL 4H DIFORMYLPYRAN DERIVATIVE; ACETAL; ALDEHYDE; ALUMINUM CHLORIDE; FERROUS CHLORIDE; LEWIS ACID; N,N DIMETHYLACETAMIDE; N,N DIMETHYLFORMAMIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; SYNTHESIS;

EID: 79953024904     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259681     Document Type: Article

References (26)

1. For recent examples, see:, Oepstad C L., Sliwka H.-R, Partali V, Eur. J. Org. Chem. 2010 435
2. Fan X, Feng D, Qu Y, Zhang X, Wang J, Loiseau P M., Andrei G, Snoeck R, De Clercq E, Bioorg. Med. Chem. Lett. 2010 20 809
3. Aljarilla A, Plumet J, Heterocycles 2008 76 827
4. Lachance H, Marion O, Hall D G., Tetrahedron Lett. 2008 49 6061
5. Salit A.-F, Meyer C, Cossy J, Synlett 2007 934
6. Li W, Wayne G S., Lallaman J E., Wittenberger S J., J. Org. Chem. 2006 71 1725
7. Donner C D., Gill M, Tewierik L M., Molecules 2004 9 498
8. Tanaka S, Isobe M, Tetrahedron 1994 50 5633
9. Crawley G C., Briggs M T., Dowell R I., Edwards P N., Hamilton P M., Kingston J F., Oldham K, Waterson D, Whalley D P., J. Med. Chem. 1993 36 295
10. Zhang X.-M, Tu Y.-Q, Jiang Y.-J, Zhang Y.-Q, Fan C.-A, Zhang F.-M, Chem. Commun. 2009 4726
11. Hoye T R., Danielson M E., May A E., Zhao H, Angew. Chem. Int. Ed. 2008 47 9743
12. Foroumadi A, Emami S, Sorkhi M, Nakhjiri M, Nazarian Z, Heydari S, Ardestani S K., Poorrajab F, Shafiee A, Chem. Biol. Drug Des. 2010 75 590
13. Shaabani A, Nejat F S., J. Chem. Res., Synop. 1998 584
14. Amaresh R R., Perumal P T., Tetrahedron 1999 55 8083
15. Csihony S, Mika L, Vlád G, Barta K, Mehnert C P., Horváth I T., Collect. Czech. Chem. Commun. 2007 72 1094; and references therein
16. Reichardt C, Yun K.-Y, Massa W, Schmidt R E., Liebigs Ann. Chem. 1985 1987
17. Medvedeva A S., Pavlov D V., Mareev A V., Russ. J. Org. Chem. 2008 44 143
18. Maeda S, Obora Y, Ishii Y, Eur. J. Org. Chem. 2009 4067
19. Tamaso K, Hatamoto Y, Sakaguchi S, Obora Y, Ishii Y, J. Org. Chem. 2007 72 3603
20. Tamaso K, Hatamoto Y, Obora Y, Sakaguchi S, Ishii Y, J. Org. Chem. 2007 72 8820
21. Maeda S, Horikawa N, Obora Y, Ishii Y, J. Org. Chem. 2009 74 9558
22. Cockerill A F., Harrison R G., In The Chemistry of Double-Bonded Functional Groups Part 1 Patai S John Wiley and Sons London 1977 277-285
23. Oare D A., Heathcock C H., Top. Stereochem. 1989 19 227
24. Krishtal G V., Kulganek V V., Kucherov V F., Yanovskaya L A., Synthesis 1979 107
25. Yamaguchi M, Yokota N, Minami T, J. Chem. Chem., Chem. Commun. 1991 1088
26. Oare D A., Heathcock C H., Top. Stereochem. 1991 20 87