Facile entry to 4- and 5-hydroxybenzofuran and to their amino derivatives

Synthetic Communications

Volumn 36, Issue 14, 2006, Pages 1983-1990

  Bonini, Carlo ^a   Cristiani, Graziella ^a   Funicello, Maria ^a   Viggiani, Licia ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

4 hydroxybenzofuran; Aminobenzo condensed derivatives; Smiles rearrangement

Indexed keywords

4 HYDROXYBENZOFURAN; 5 HYDROXYBENZOFURAN; AMINO ACID DERIVATIVE; BENZOFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CYCLIZATION; DEMETHYLATION; DERIVATIZATION; DRUG ISOLATION; ENZYME INHIBITION; REACTION ANALYSIS; SYNTHESIS;

EID: 33745302596     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600634118     Document Type: Article

References (25)

1. Rouzer, C. A.; Riendau, D.; Falgueyret, J. P.; Lau, C. K.; Gresser, M. J. Inhibition of human leukocyte 5-lipoxygenase by a 4-hydroxybenzofuran, L-656,224: Evidence for enzyme reduction and inhibitor degradation. Biochem. Pharmacol. 1991, 41, 1365-1373.
2. Bosin, T. R.; Campaigne, E. E. Biologically active benzo[b]thiophene derivatives, II: Adv. Drug. Res. 1977, 11, 191-232.
3. For 4-hydroxybenzofuran, see (a) Kneen, G.; Maddocks, P. J. A convenient synthesis of 4-hydroxybenzo(b)furan, (karanjol). Synth. Commun. 1986, 16, 1635-1640;
4. (b) Royer, R.; René, L. Recherches sur le benzofuranne: Sur une nouvelle voie d'access aux hydroxy benzofurannes. Bull. Soc. Chim. Fr. 1973, 2355-2356;
5. For reported synthesis of 5-methoxybenzofuran, see (c) Barker, P.; Finke, P.; Thompson, K. Preparation and cyclization of aryloxyacetaldehyde acetals: A general synthesis of 2,3-unsubstituted benzofurans. Synth. Commun. 1989, 19, 257-265.
6. Li, W.-S.; Guo, Z.; Thornton, J.; Katipally, K.; Polniaszek, R.; Thottathil, J.; Vu, T.; Wong, M. Synthesis of substituted 2,3-dihydrobenzofuran in a process involving a facile acyl migration. Tetrahedron Lett. 2002, 43, 1923-1925.
7. Bonini, C.; Funicello, M.; Scialpi, R.; Spagnolo, P. Smiles rearrangement for the synthesis of 5-amino-substituted[1]benzothieno[2,3-b]pyridine. Tetrahedron 2003, 59, 7515-7520.
8. Mukherjee, S.; Jash, S. S.; De, A. Studies in sulfur heterocycles, part 8: 3,4-Dihydro-thieno[2,3-i][1]benzoxepin-5(2H)-one, a new heterocyclic system and a key intermediate in the synthesis of novel polycondensed sulfur heterocycles. J. Chem Res., Synop. 1993, 192-193.
9. For deprotection of aryl- and heteroaryl methyl ethers (a) Wipf, P.; Jung, J.-K. Formal total synthesis of (+) diepoxin σ. J. Org. Chem. 2000, 65, 6319-6337;
10. (b) Bernard, A. M.; Ghiani, M. R.; Piras, P. P.; Rivoldini, A. Dealkylation of activated alkyl aryl ethers using lithium chloride in dimethylformamide. Synthesis 1989, 287-289;
11. (c) Williard, P. G.; Fryhle, C. B. Boron trihalide-methyl sulfide complexes as convenient reagents for dealkylation of aryl ethers. Tetrahedron Lett. 1980, 21, 3731-3734;
12. (d) Royer, R.; Bursson, P.; Demerseman, P.; Lechartier, J.-P. Reactions induites par le chlorhydrate de pyridine. Etude des conditions de la desalcoylation des ethers phenolique: cas du methoxy-2-naphtalene. Bull. Soc. Chim. Fr. 1969, 2792-2797;
13. (e) McOmie, J. F. W.; Watts, M. L.; West, D. E. Demethylation of aryl methyl ethers by boron tribromide. Tetrahedron 1968, 24, 2289-2292.
14. (a) Plé, P. A.; Green, T. P.; Hennequin, L. F.; Curwen, J.; Fennel, M.; Allen, J.; Lambert-van der Brempt, C.; Costello, G. Discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of c-Src. J. Med. Chem. 2004, 47, 871-887;
15. (b) Eissenstat, M. A.; Bell, M. R.; D'Ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G. Aminoalkylindoles: Structure-activity relationships of novel cannabinoid mimetics. J. Med. Chem. 1995, 38, 3094-3105.
16. Scherrer, R. A.; Beatty, H. R. General conversion of phenols to anilines. J. Org. Chem. 1972, 37, 1681-6.
17. Rossi, R. A.; Bunnett, J. F. Dehydroxylation of phenols by cleavage of their diethyl phosphate esters with alkali metals in liquid ammonia. J. Org. Chem. 1973, 38, 2314-2318.
18. Rieche, A.; Seeboth, H. Mechanism of the Bucherer reaction. Ang. Chem. 1958, 70, 52-312;
19. (b) Smith, M. B.; March, J. March's Advanced Organic Chemistry; Wiley: New York, 2001; chap 13 p. 865.
20. Bayles, R.; Johnson, M. C.; Maisey, R. F.; Turner, R. W. A Smiles rearrangement involving non-activated aromatic systems: The facile conversion of phenols to anilines. Synthesis 1977, 33-34.
21. Coutts, I. G. C.; Southcott, M. R. The conversion of phenols to primary and secondary aromatic amines via a Smiles rearrangement. J. Chem. Soc., Perkin Trans. 1990, 1, 767-771.
22. Mizuno, M.; Yamano, M. A new practical one-pot conversion of phenols to anilines. Org. Lett. 2005, 7, 3629-3631.
23. Weidner, J. J.; Peet, N. P. Direct conversion of hydroxy aromatic compounds to heterorylamines via a one-pot Smiles rearrangement procedure. J. Heterocycl. Chem. 1997, 34, 1857-1860.
24. (a) Boschi, D.; Sorba, G.; Bertinaria, M.; Fruttero, R.; Calvino, R.; Gasco, A. Unsymmetrically substituted furoxans, part 18: Smiles rearrangement in furoxan systems and in related furazans. J. Chem. Soc., Perkin Trans. 1 2001, 1751;
25. (b) Hirota, T.; Tomita, K.; Sasaki, K.; Okuda, K.; Yoshida, M.; Kashino, S. Polycyclic N-heterocyclic compounds: Syntheses of fused furo (or thieno) [2,3-b] pyridine derivatives via Smiles rearrangement and cyclization. Heterocycles 2001, 55, 741-752.