Implementation of a combinatorial cleavage and deprotection scheme. 1. Synthesis of phthalhydrazide libraries

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3351-3354

  Nielsen, John ^a   Rasmussen, Palle H ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZIDE; PHTHALIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029880074     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00544-8     Document Type: Article

References (19)

1. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem.1994, 37, 1233-1251.
2. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem.1994, 37, 1385-1401.
3. Nielsen, J. Chemistry & Industry 1994, 902-905.
4. (a) Pirrung, M.C.; Chen, J. J. Am. Chem. Soc. 1995. 117, 1240-1245.
5. (b) Pirrung, M.C.; Chau, J.H.-L.; Chen, J. Chemistry & Biology 1995, 2, 621-626.
6. Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chemistry & Biology 1995. 2, 171-183.
7. (a) Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. In 14th Int. Congr. Biochem. 1988. Praque, Czechchoslovakia: W. de Gruyter: Berlin/New York 1989.
8. (b) Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. In 10th Int. Symp. Med. Chem. 1988. Budapest, Hungary: Elsevier: Amsterdam/New York 1989.
9. Lam, K.S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature, 1991, 354, 82-84.
10. See e.g. (a) Bunin, B. A. and Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-10998.
11. (b) Bunin, B. A., Plunkett, M. J. and Ellman, J. A. Proc. Natl. Acad. Sci. USA. 1994, 91, 4708-4712.
12. (a) Plunkett, M. J. and Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007.
13. (b) Chenera, B., Finkelstein, J. A. and Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
14. During the course of this work, a paper describing the application of 3 different reaction conditions on one common synthon appeared: Ley, S.V.; Mynett, D.M.; Koot, W.-J. Synlett. 1995, 1017-1020.
15. Ing, H. R.; Manske, R. H. F. J. Chem. Soc. 1926, 2348-2351.
16. Murthy, A. R. K.; Hall, I. H.; Chapman, J. M.; Rhyne, K. A.; Wyrick, S. D. Pharm. Res. 1986, 3, 93-101.
17. Hall, I. H.; Hall, E. S.; Wong, O. T. Anti-Cancer Drugs 1992, 3, 55-62.
18. Some hydrazines are available only as the mono-or dihydrochloride, for which reason 3 eq. of catalyst (DIPEA) is preferable.
19. Weinshenker, N. M; Shen, C. M.; Wong, J. Y. Org. Synth. 1988, Coll. Vol. 6, 951-954.