Solid-supported chloro[1,3,5]triazine. A versatile new synthetic auxiliary for the synthesis of amide libraries

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1355-1357

  Masala, Simonetta ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000482297     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990215h     Document Type: Article

References (26)

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5. Paio, A.; Zaramella, A.; Ferritto, R.; Conti, N.; Marchioro, C.; P. Seneci J. Comb. Chem. 1999, 1, 317. Hu, Y.; Baudart, S.; Porco, J. A., Jr. J. Org. Chem. 1999, 64, 1049. Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491. Minutolo, F.; Katzenellenbogen J. A. Angew. Chem. Int. Ed. Engl. 1999, 38, 1617. Hamuro, Y.; Scialdone, M. A.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 1636. Ley, S. V.; Bolli, M. H.; Hinzen, B.; Gervois, A.-G.; Hall B. J. J. Chem. Soc., Perkin Trans. 1 1998, 2239.
6. Paio, A.; Zaramella, A.; Ferritto, R.; Conti, N.; Marchioro, C.; P. Seneci J. Comb. Chem. 1999, 1, 317. Hu, Y.; Baudart, S.; Porco, J. A., Jr. J. Org. Chem. 1999, 64, 1049. Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491. Minutolo, F.; Katzenellenbogen J. A. Angew. Chem. Int. Ed. Engl. 1999, 38, 1617. Hamuro, Y.; Scialdone, M. A.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 1636. Ley, S. V.; Bolli, M. H.; Hinzen, B.; Gervois, A.-G.; Hall B. J. J. Chem. Soc., Perkin Trans. 1 1998, 2239.
7. Paio, A.; Zaramella, A.; Ferritto, R.; Conti, N.; Marchioro, C.; P. Seneci J. Comb. Chem. 1999, 1, 317. Hu, Y.; Baudart, S.; Porco, J. A., Jr. J. Org. Chem. 1999, 64, 1049. Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491. Minutolo, F.; Katzenellenbogen J. A. Angew. Chem. Int. Ed. Engl. 1999, 38, 1617. Hamuro, Y.; Scialdone, M. A.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 1636. Ley, S. V.; Bolli, M. H.; Hinzen, B.; Gervois, A.-G.; Hall B. J. J. Chem. Soc., Perkin Trans. 1 1998, 2239.
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11. Huang, W.; Kalivretenos, A. G. Tetrahedron Lett. 1995, 36, 9113. Dendrinos, K.; Jeong, J.; Huang, W.; Kalivretenos, A. G. J. Chem. Soc., Chem. Commun. 1998, 499.
12. Huang, W.; Kalivretenos, A. G. Tetrahedron Lett. 1995, 36, 9113. Dendrinos, K.; Jeong, J.; Huang, W.; Kalivretenos, A. G. J. Chem. Soc., Chem. Commun. 1998, 499.
13. Kalir, R.; Warshawsky, A. Fridkin, M.; Patchornik, A. Eur. J. Biochem. 1975, 59, 55.
14. The polymer-supported bis(6-carboxy-HOBt)-N-(2-ammoethyl)aminomethyl polystyrene and N-cyclohexylcarbodiimide N′-methyl polystyrene are now available from Novabiochem, catalog no. 01-64-0179 and 01-64-0211.
15. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395.
16. Venkataram, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037. Kaminski, Z. J. Synthesis 1987, 917. Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599. Nayar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
17. Venkataram, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037. Kaminski, Z. J. Synthesis 1987, 917. Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599. Nayar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
18. Venkataram, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037. Kaminski, Z. J. Synthesis 1987, 917. Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599. Nayar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
19. Venkataram, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037. Kaminski, Z. J. Synthesis 1987, 917. Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599. Nayar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
20. Venkataram, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037. Kaminski, Z. J. Synthesis 1987, 917. Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599. Nayar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
21. Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248.
22. The correct loading of 1 on the resin (one triazine ring for one amino group) was confirmed by the contents of Cl and N determined by microanalysis.
23. The selective substitution of one single chlorine with the carboxylate was verified by FT-IR analysis of the beads and by micronalysis.
24. The presence of NMM in the reaction is necessary. Attempts to use less than 1 equiv of the desired amine and to obtain a solution of the pure product at the end of the reaction were unsuccessfull (in our hands).
25. The classical two-phase extraction with an acidic aqueous solution can be substituted by a passage of the THF solution, coming from the vial, through a small column filled with an acidic ion-exchange resin. After this treatment the amide could be recovered by evaporation of the solvent with an acceptable level of purity. See: Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513.
26. Chlorotriazines containing one NH group are reported to be hydrolyzed in acidic aqueous medium. Thurston, J. T.; Dudley, J. R.; Kaiser, D. W.; Hechenbleikner, I.; Schaefer, F. C.; Holm-Hansen, D. J. Am. Chem. Soc. 1951, 73, 2981.