General and efficient protocol for formylation of aromatic and heterocyclic phenols

Synthesis (Germany)

Volumn 44, Issue 23, 2012, Pages 3683-3687

  Skonieczny, Kamil ^a   Charalambidis, Georgios ^b   Tasior, Mariusz ^a   Krzeszewski, MacIej ^c   Kalkan Burat, Ayfer ^a   Coutsolelos, Athanassios G ^b   Gryko, Daniel T ^a,c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF CRETE   (Greece)

^c WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

aldehydes; arenes; electrophilic aromatic substitution; heterocycles; phenols

Indexed keywords

ARENES; DIALDEHYDES; DIVERSE RANGE; ELECTROPHILIC AROMATIC SUBSTITUTIONS; FORMYLATION; HETEROCYCLES;

ALDEHYDES;

PHENOLS;

3,5 DI TERT BUTYL 2,4 DIHYDROXYISOPHTHALALDEHYDE; 3,5 DICHLORO 2,6 DIHYDROBENZALDEHYDE; 4 FORMYL 2 HEXYL 3 HYDROXY 6H DIBENZO[B,D]PYRAN 6 ONE; 4,6 DIHYDROXY 5 METHYLISOPHTHALALDEHYDE; 4,6 DIHYDROXY 5 NITROISOPHTHALALDEHYDE; 5 (TERT BUTYL) 2,4 DIHYDROXYISOPHTHALALDEHYDE; 5 ETHYL 2,4 DIHYDROXYISOPHTHALALDEHYDE; 5 HEXYL 2,4 DIHYDROXYISOPHTHALALDEHYDE; 5 HYDROXY 2,3 DIPHENYLBENZOFURAN 4,7 DICARBALDEHYDE; 5,7 DIFORMYL 5 HYDROXYQUINOLINE 1 OXIDE; 6 HYDROXY 2,3 DIPHENYL 1 BENZOFURAN 5,7 DICARBALDEHYDE; ETHYL FORMYL 3 HYDROXYPYRIDO[1,2 A]INDOLE 10 CARBOXYLATE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; FORMYLATION; PROCESS OPTIMIZATION; SYNTHESIS; TEMPERATURE;

EID: 84870251902     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1317500     Document Type: Article

References (28)

1. Jutz C. Adv. Org. Chem.: 1976; 9 225
2. Gattermann L., Koch J. A. Ber. Dtsch. Ges. Chem.: 1897; 30 1622
3. Wynberg H., Meijer E. W. Org. React.: 1982; 28 2
4. Wynberg H. In Comprehensive Organic Synthesis. Vol. 2 Trost B. M., Fleming I. Pergamon Press Oxford: 1991; 769 775
5. Kantlehner W. Eur. J. Org. Chem.: 2003; 2530
6. Casiraghi G., Casnati G., Puglia G., Sartori G., Terenghi G. J. Chem. Soc., Perkin Trans. 1: 1980; 1862
7. Aldred R., Johnston R., Levin D., Neilan J. J. Chem. Soc., Perkin Trans. 1: 1994; 1823
8. Sashidhara K. V., Kumar A., Kumar M., Srivastava A., Puri A. Bioorg. Med. Chem. Lett.: 2010; 20 6504
9. Sashidhara K. V., Kumar A., Chatterjee M., Rao K. B., Singh S., Verma A. K., Palit G. Bioorg. Med. Chem. Lett.: 2011; 21 1937
10. Chen W-H, Xing Y., Pang Y. Org. Lett.: 2011; 13 1362
11. Dong Y., Li J., Jiang X., Song F., Cheng Y., Zhu C. Org. Lett.: 2011; 13 2252
12. Duff J. C., Bills E. J. J. Chem. Soc.: 1932; 1987
13. Duff J. C., Bills E. J. J. Chem. Soc.: 1934; 1305
14. Duff J. C., Bills E. J. J. Chem. Soc.: 1941; 547
15. Duff J. C., Bills E. J. J. Chem. Soc.: 1945; 276
16. Chong J. H., Sauer M., Patrick B. O., MacLachlan M. J. Org. Lett.: 2003; 5 3823
17. Yelamaggad C. V., Achalkumar A. S., Rao D. S. S, Prasad S. K. J. Org. Chem.: 2009; 74 3168
18. Yelamaggad C. V., Prabhu R., Rao D. S. S, Prasad K. Tetrahedron Lett.: 2010; 51 4579
19. Anderson A. A., Goetzen T., Shackelford S. A., Tsank S. Synth. Commun.: 2000; 30 3227
20. Sashidhara K. V., Rosaiah J. N., Narender T. Tetrahedron Lett.: 2007; 48 1699
21. Ieda N., Nakagawa H., Horinouchi T., Peng T., Yang D., Tsumoto H., Suzuki T., Fukuhara K., Miyata N. Chem. Commun.: 2011; 47 6449
22. Yaseen M., Ali M., NajeebUllah M., Munawar M. A., Khokhara I. J. Heterocycl. Chem.: 2009; 46 251
23. Hryniewicka A., Morzycki J. W., Witkowski S. J. Organomet. Chem.: 2010; 695 1265
24. Nielsen M., Thomsen A. H., Clo M., Kirpekar F., Gothelf K. V. J. Org. Chem.: 2004; 69 2240
25. Sabater L., Guillot R., Aukauloo A. Tetrahedron Lett.: 2005; 46 2923
26. Shopsowitz K. E., Edwards D., Gallant A. J., MacLachlan M. J. Tetrahedron: 2009; 65 8113
27. Hudecek O., Curinova P., Budka J., Lhoták P. Tetrahedron: 2011; 67 5213
28. Fkyerat A., Dubin G.-M, Tabacchi R. Helv. Chim. Acta: 1999; 82 1418