Convenient regioselective functionalization at the upper-rim of p-tert-butylcalix[8]arene through a protection-deprotection procedure

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8875-8878

  Gaeta, Carmine ^a   Gregoli, Luisa ^a   Martino, Marco ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Calix 8 arenes; Calixarenes; Protection deprotection; Upper rim functionalization

Indexed keywords

4 TERT BUTYLCALIX[4]ARENE; AROMATIC COMPOUND; BRIDGED COMPOUND; CALIXARENE; FUNCTIONAL GROUP; HYDROGEN; HYDROQUINONE DERIVATIVE; NITRO DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; METHODOLOGY; SYNTHESIS;

ARENE;

EID: 0037010813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02204-9     Document Type: Article

References (26)

1. For general reviews on calixarenes, see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713
2. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998
3. Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens J.; Eds.; Kluwer: Dordrecht, 2001.
4. Atwood J.L., Koutsantonis G.A., Raston C.L. Nature. 368:1994;229.
5. Suzuki T., Nakashima K., Shinkai S. Chem. Lett. 1994;699
6. See Ref. 1c: Zhong, Z.-L.; Ikeda, A.; Shinkai, S.; Chapter 26, pp. 476-495.
7. Ikeda A., Akao K., Harada T., Shinkai S. Tetrahedron Lett. 37:1996;1621.
8. Ikeda A., Suzuki Y., Akao K., Shinkai S. Chem. Lett. 1996;963.
9. Geraci C., Chessari G., Piattelli M., Neri P. Chem. Commun. 1997;921.
10. Casnati A., Barboso S., Rouquette H., Schwing-Weill M.-J., Arnaud-Neu F., Dozol J.-F., Ungaro R. J. Am. Chem. Soc. 123:2001;12182.
11. See Ref. 1c, Chapter 5, pp. 89-109.
12. Bottino A., Cunsolo F., Piattelli M., Garozzo D., Neri P. J. Org. Chem. 64:1999;8018.
13. Tsue, H.; Ohmori, M.; Hirao, K. J. Org. Chem. 1998, 63, 4866.
14. For a study on the formation of the numerous by-products of this reaction, see: Tsue, H.; Enyo, K.; Hirao, K. Org. Lett. 2000, 2, 3071.
15. Tsue, H.; Enyo, K.; Hirao, K. Helv. Chim. Acta 2001, 84, 849.
16. van Loon J.D., Arduini A., Coppi L., Verboom W., Pochini A., Ungaro R., Harkema S., Reinhoudt D.N. J. Org. Chem. 55:1990;5639.
17. de Mendoza J., Carramolino M., Cuevas F., Nieto P.M., Prados P., Reinhoudt D.N., Verboom W., Ungaro R., Casnati A. Synthesis. 00:1994;47.
18. Cunsolo F., Piattelli M., Neri P. J. Chem. Soc., Chem. Commun. 1994;1917.
19. Cunsolo F., Consoli G.M.L., Piattelli M., Neri P. Tetrahedron Lett. 37:1996;715.
20. Geraci C., Piattelli M., Chessari G., Neri P. J. Org. Chem. 65:2000;5143.
21. Consoli G.M.L., Cunsolo F., Geraci C., Neri P. Org. Lett. 3:2001;1605.
22. 3 (1.0 g, 3.08 mmol) under stirring. The mixture was kept under stirring at 70°C for 2 h and then a solution of 1,2-, 1,3-, or 1,4-bis(bromomethyl)benzene (0.75, 0.75, and 0.77 mmol, respectively) in DMF (4 ml) was added dropwise. The reaction was stirred at 70°C for 24-36 h. After concentration under vacuum, the residue was triturated with 1N HCl (100 ml), collected by filtration, washed with MeOH and dried. Analytically pure samples were obtained by crystallization or by chromatography on silica gel.
23. 2Ar, 8H, 8H), 6.48, 7.05 (s, ArH, 4H, 4H), 6.97, 7.08 (d, J=2.4 Hz, 4H, 4H), 7.24, 7.40 (s, OH, 2H, 2H).
24. Compound 2c was previously obtained in 13% yield by Shinkai and co-workers, by direct alkylation of 1 in the presence of NaH (see Ref. 3a ).
25. Neri P., Geraci C., Piattelli M. J. Org. Chem. 60:1995;4126.
26. Consoli G.M.L., Cunsolo F., Geraci C., Gavuzzo E., Neri P. Org. Lett. 4:2002;2649.