Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds

Organic Letters

Volumn 7, Issue 3, 2005, Pages 467-470

  Pettigrew, Jeremy D ^a   Cadieux, Jay A ^a   So, Simon S S ^a   Wilson, Peter D ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENEBORONIC ACID; CARBONYL DERIVATIVE; CHOLINESTERASE INHIBITOR; CHROMENE DERIVATIVE; FUNGAL PROTEIN; PHLOROGLUCINOL; UNCLASSIFIED DRUG; XYLOKETAL A;

ARTICLE; CHEMICAL STRUCTURE; POLYMERIZATION;

ACETYLCHOLINESTERASE; BENZOPYRANS; BORONIC ACIDS; CATALYSIS; CHOLINESTERASE INHIBITORS; PHLOROGLUCINOL; PYRANS;

EID: 13844272573     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047578o     Document Type: Article

References (24)

1. Lin, Y.; Wu, X.; Feng, S.; Jiang, G.; Luo, J.; Zhou, S.; Vrijmoed, L. L. P.; Jones, E. B. G.; Krohn, K.; Steingröver, K.; Zsila, F. J. Org. Chem. 2001, 66, 6252.
2. (a) Pettigrew, J. D.; Bexrud, J. A.; Freeman, R. P.; Wilson, P. D. Heterocycles 2004, 62, 445.
3. (b) Pettigrew, J. D.; Freeman, R. P.; Wilson, P. D. Can. J. Chem. 2004, 82, 1640.
4. (a) Krohn, K.; Riaz, M. Tetrahedron Lett. 2004, 45, 293.
5. (b) Krohn, K.; Riaz, M.; Flörke, U. Eur. J. Org. Chem. 2004, 1261.
6. For reviews on the synthesis of 2H-chromene derivatives, see: (a) Merlini, L. Adv. Heterocycl. Chem. 1975, 18, 159. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 737-883. (c) Lévai, A.; Tímár, T.; Sebök, P.; Eszenyi, T. Heterocycles 2000, 53, 1193. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734 and references therein. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939 and references therein.
7. For reviews on the synthesis of 2H-chromene derivatives, see: (a) Merlini, L. Adv. Heterocycl. Chem. 1975, 18, 159. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 737-883. (c) Lévai, A.; Tímár, T.; Sebök, P.; Eszenyi, T. Heterocycles 2000, 53, 1193. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734 and references therein. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939 and references therein.
8. For reviews on the synthesis of 2H-chromene derivatives, see: (a) Merlini, L. Adv. Heterocycl. Chem. 1975, 18, 159. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 737-883. (c) Lévai, A.; Tímár, T.; Sebök, P.; Eszenyi, T. Heterocycles 2000, 53, 1193. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734 and references therein. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939 and references therein.
9. For reviews on the synthesis of 2H-chromene derivatives, see: (a) Merlini, L. Adv. Heterocycl. Chem. 1975, 18, 159. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 737-883. (c) Lévai, A.; Tímár, T.; Sebök, P.; Eszenyi, T. Heterocycles 2000, 53, 1193. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734 and references therein. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939 and references therein.
10. For reviews on the synthesis of 2H-chromene derivatives, see: (a) Merlini, L. Adv. Heterocycl. Chem. 1975, 18, 159. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 737-883. (c) Lévai, A.; Tímár, T.; Sebök, P.; Eszenyi, T. Heterocycles 2000, 53, 1193. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734 and references therein. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939 and references therein.
11. Our preliminary investigations also involved the use of calcium hydroxide in methanol (Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa, H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768), magnesium sulfate and allylamine in tetrahydrofuran (Paduraru, M. P.; Wilson, P. D. Org. Lett. 2003, 5, 4911), and calcium chloride hydrate and triethylamine in ethanol (Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481) as reagents. However, these reactions afforded complex mixtures of products that contained only trace amounts of compounds 10 and 11.
12. Our preliminary investigations also involved the use of calcium hydroxide in methanol (Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa, H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768), magnesium sulfate and allylamine in tetrahydrofuran (Paduraru, M. P.; Wilson, P. D. Org. Lett. 2003, 5, 4911), and calcium chloride hydrate and triethylamine in ethanol (Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481) as reagents. However, these reactions afforded complex mixtures of products that contained only trace amounts of compounds 10 and 11.
13. Our preliminary investigations also involved the use of calcium hydroxide in methanol (Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa, H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768), magnesium sulfate and allylamine in tetrahydrofuran (Paduraru, M. P.; Wilson, P. D. Org. Lett. 2003, 5, 4911), and calcium chloride hydrate and triethylamine in ethanol (Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481) as reagents. However, these reactions afforded complex mixtures of products that contained only trace amounts of compounds 10 and 11.
14. For references on the use of phenylboronic acid to prepare 2H-chromenes, see: (a) Bissada, S.; Lau, C. K.; Bernstein, M. A.; Dufresne, C. Can. J. Chem. 1994, 72, 1866. (b) Chauder, B. A.; Lopes, C. C.; Lopes, R. S. C.; da Silva, A. J. M.; Snieckus, V. Synthesis 1998, 279.
15. For references on the use of phenylboronic acid to prepare 2H-chromenes, see: (a) Bissada, S.; Lau, C. K.; Bernstein, M. A.; Dufresne, C. Can. J. Chem. 1994, 72, 1866. (b) Chauder, B. A.; Lopes, C. C.; Lopes, R. S. C.; da Silva, A. J. M.; Snieckus, V. Synthesis 1998, 279.
16. For references regarding the pioneering use of boric acid and phenylboronic acid in ortho-selective electrophilic aromatic substitution reactions of phenols with aldehydes, see: (a) Peer, H. G. Recl. Trav. Chim. Pays-Bas 1960, 79, 825. (b) Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365 and references therein.
17. For references regarding the pioneering use of boric acid and phenylboronic acid in ortho-selective electrophilic aromatic substitution reactions of phenols with aldehydes, see: (a) Peer, H. G. Recl. Trav. Chim. Pays-Bas 1960, 79, 825. (b) Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365 and references therein.
18. Heating phloroglucinol 7 (1 equiv) with senecialdehyde 9 (4 equiv) and propionic acid in toluene at 80°C, without the azeotropic removal of water (or in the presence of 4 Å molecular sieves), only afforded trace amounts of the desired products 10 and 11.
19. For additional discussion on the "ortho-specific" electrophilic aromatic substitution reaction of phenols with aldehydes via 1,3,2-benzodioxaborins, see: Lau, C. K.; Williams, H. W. R.; Tardiff, S.; Dufresne, C.; Scheigetz, J.; Bélanger, P. C. Can. J. Chem. 1989, 67, 1384.
20. (a) Wolfrom, M. L.; Wildi, B. S. J. Am. Chem. Soc. 1951, 73, 235.
21. (b) Al-Khayat, I.; Dean, F. M.; Parvizi, B.; Sutcliffe, L. H. J. Chem. Soc., Chem. Commun. 1979, 213.
22. The aldehydes 16-18 were prepared in three steps from cyclopentanone, cyclohexanone and adamantanone, based on a literature procedure; see: Snowden, R. L.; Linder, S. M.; Würst, M. Helv. Chim. Acta 1989, 72, 892.
23. The aldehyde 20 was prepared in four steps from 1-methylcyclohexene on modification of a literature procedure; see: (a) White, J. D.; Ruppert, J. F.; Avery, M. A.; Torii, S.; Nokami, J. J. Am. Chem. Soc. 1981, 103, 1813. (b) Hudlicky, T.; Ranu, B. C.; Naqvi, S. M.; Srnak, A. J. Org. Chem. 1985, 50, 123.
24. The aldehyde 20 was prepared in four steps from 1-methylcyclohexene on modification of a literature procedure; see: (a) White, J. D.; Ruppert, J. F.; Avery, M. A.; Torii, S.; Nokami, J. J. Am. Chem. Soc. 1981, 103, 1813. (b) Hudlicky, T.; Ranu, B. C.; Naqvi, S. M.; Srnak, A. J. Org. Chem. 1985, 50, 123.