Synthesis of 2,4-Disubstituted Thiazole Combinatorial Unit on Solid-Phase: Microwave Assisted Conversion of Alcohol to Amine Monitored by FT-IR
Keywords:
Thiazole, microwave, monitoring solid-phase reactionsAbstract
Abstract. Microwave-assisted solid-phase synthesis of the 2,4-disubstituted thiazole 3 on Merrifield Resin is described. The hydroxyl moiety was converted to amine in five steps – including coupling and
cleavage – within a total reaction time of 2 hours and 26% overall yield. The entire solid-phase synthesis was efficiently monitored by FT-IR/KBr pellets and allows potential use in combinatorial chemistry.
Downloads
Download data is not yet available.
References
1. Winter, M.; Warrass, R. In Combinatorial Chemistry Practical Approach; H. Fenniri, ed.; Oxford University Press: Oxford, 2000, ch. 6, and references therein.
2. Graebin, C. S.; Eifler-Lima, V. L.; Quim. Nova. 2005, 28, 73.
3. Lorgé, F.; Wagner, A.; Mioskowski, C.; J. Comb. Chem. 1999, 1, 25; Rousselot-Pailley, P.; Ede, N. J.; Lippens, G.; J. Comb. Chem. 2001, 3, 559; Grice, P.; Leach, A. G.; Ley, S. V.; Massi, A.; Mynett, D. M.; J. Comb. Chem. 2000, 2, 491; Yan, B.; Li, W.; J. Org. Chem. 1997, 62, 9354.
4. Yan, B.; Gremlich, H. U.; J. Chromatography B. 1999, 725, 91; Yan, B.; Gremlich, H. U.; Moss, S.; Coppola, G. M.; Sun, Q.; Liu, L.; J. Comb. Chem. 1999, 1, 46.
5. Groweiss, A.; Shmueli, U.; Kashman, Y.; Tetrahedron Lett. 1980, 21, 3629; Okuda, R.; Sheuer, P. J.; Experientia 1985, 41, 1355; Kashman, Y.; Groweiss, A.; Lidor, R.; Blasberger, D.; Carmely, S.; Tetrahedron 1985, 41, 1905; Blasberger, D.; Carmely, S.; Cojocaru, M.; Spector, I.; Shochet, N. R.; Kashman, Y.; Liebigs Ann. Chem. 1989, 1171; Northcote, P.; Blunt, J. W.; Munro, M. H.; Tetrahedron Lett. 1991, 32, 6411; Kobayashi, J.; Kondo, K.; Ishibashi, M.; Wälchli, M. R.; Nakamura, T.; J. Am. Chem. Soc. 1993, 115, 6661; Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamet, E.; Blokkin, A.; State, D.; J. Org. Chem. 1994, 59, 1243.
6. Crews, P.; Kakaou, Y.; Quiñoa, E.; J. Am. Chem. Soc. 1988, 110, 4365.
7. Antonow, D.; Graebin, C. S.; Eifler-Lima, V. L.; J. Braz. Chem. Soc. 2004, 15, 782.
8. Mahler, S. G.; Serra, G. L.; Antonow, D.; Manta, E.; Tetrahedron Lett. 2001, 42, 8143.
9. Gisin, B. F.; Helv. Chim. Acta. 1973, 56, 1476; Anuradha, M. V.; Ravindranath, B.; Tetrahedron 1995, 51, 5671.
10. Salunkhe, A. M.; Ramachandran, P. V.; Brown, H. C.; Tetrahedron 2002, 58, 10059; Bosch, I.; Costa, A. M.; Martin, M.; Urpi, F.; Vilarrasa, J.; Org. Lett. 2000, 2, 397; Ding, J. C.; Wu, H. Y.; Chin. Chem. Lett. 2001, 12, 662; Kamal, A.; Reddy, G. S. K.; Reddy, K. L.; Tetrahedron Lett. 2001, 42, 6969; Kamal, A.; Reddy, K. S.; Prasad, B. R.; Babu, A. H.; Ramana, A. V.; Tetrahedron Lett. 2004, 45, 6517.
11. Frenette, R.; Friesen, R. W.; Tetrahedron Lett. 1994, 35, 9177.
12. Perrin, D. D.; Armarego, W. L. F.; Purification of Laboratory Chemicals, 3rd ed., Pergamon Press: Oxford, 1988.
2. Graebin, C. S.; Eifler-Lima, V. L.; Quim. Nova. 2005, 28, 73.
3. Lorgé, F.; Wagner, A.; Mioskowski, C.; J. Comb. Chem. 1999, 1, 25; Rousselot-Pailley, P.; Ede, N. J.; Lippens, G.; J. Comb. Chem. 2001, 3, 559; Grice, P.; Leach, A. G.; Ley, S. V.; Massi, A.; Mynett, D. M.; J. Comb. Chem. 2000, 2, 491; Yan, B.; Li, W.; J. Org. Chem. 1997, 62, 9354.
4. Yan, B.; Gremlich, H. U.; J. Chromatography B. 1999, 725, 91; Yan, B.; Gremlich, H. U.; Moss, S.; Coppola, G. M.; Sun, Q.; Liu, L.; J. Comb. Chem. 1999, 1, 46.
5. Groweiss, A.; Shmueli, U.; Kashman, Y.; Tetrahedron Lett. 1980, 21, 3629; Okuda, R.; Sheuer, P. J.; Experientia 1985, 41, 1355; Kashman, Y.; Groweiss, A.; Lidor, R.; Blasberger, D.; Carmely, S.; Tetrahedron 1985, 41, 1905; Blasberger, D.; Carmely, S.; Cojocaru, M.; Spector, I.; Shochet, N. R.; Kashman, Y.; Liebigs Ann. Chem. 1989, 1171; Northcote, P.; Blunt, J. W.; Munro, M. H.; Tetrahedron Lett. 1991, 32, 6411; Kobayashi, J.; Kondo, K.; Ishibashi, M.; Wälchli, M. R.; Nakamura, T.; J. Am. Chem. Soc. 1993, 115, 6661; Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamet, E.; Blokkin, A.; State, D.; J. Org. Chem. 1994, 59, 1243.
6. Crews, P.; Kakaou, Y.; Quiñoa, E.; J. Am. Chem. Soc. 1988, 110, 4365.
7. Antonow, D.; Graebin, C. S.; Eifler-Lima, V. L.; J. Braz. Chem. Soc. 2004, 15, 782.
8. Mahler, S. G.; Serra, G. L.; Antonow, D.; Manta, E.; Tetrahedron Lett. 2001, 42, 8143.
9. Gisin, B. F.; Helv. Chim. Acta. 1973, 56, 1476; Anuradha, M. V.; Ravindranath, B.; Tetrahedron 1995, 51, 5671.
10. Salunkhe, A. M.; Ramachandran, P. V.; Brown, H. C.; Tetrahedron 2002, 58, 10059; Bosch, I.; Costa, A. M.; Martin, M.; Urpi, F.; Vilarrasa, J.; Org. Lett. 2000, 2, 397; Ding, J. C.; Wu, H. Y.; Chin. Chem. Lett. 2001, 12, 662; Kamal, A.; Reddy, G. S. K.; Reddy, K. L.; Tetrahedron Lett. 2001, 42, 6969; Kamal, A.; Reddy, K. S.; Prasad, B. R.; Babu, A. H.; Ramana, A. V.; Tetrahedron Lett. 2004, 45, 6517.
11. Frenette, R.; Friesen, R. W.; Tetrahedron Lett. 1994, 35, 9177.
12. Perrin, D. D.; Armarego, W. L. F.; Purification of Laboratory Chemicals, 3rd ed., Pergamon Press: Oxford, 1988.
Downloads
Published
2020-08-07
Issue
Section
Short Report
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
