Synthesis of oxadiazoles on solid support

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8547-8550

  Hébert, Normand ^a   Hannah, Amy L ^a   Sutton, Scott C ^a  

^a Trega Biosciences Inc   (United States)

Author keywords

Combinatorial chemistry; Oxadiazoles; Solid phase synthesis

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; ACID ANHYDRIDE; NITRILE; OXIME;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; CROSS LINKING; CYCLIZATION; DEAMINATION; DRUG SYNTHESIS; REACTION ANALYSIS; SOLID;

EID: 0033520976     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01826-2     Document Type: Article

References (14)

1. Messer Jr., W. S.; Abuh, Y. F.; Liu, Y; Periyasamy, S.; Ngur, D. O.; Edgar, M. A. N.; El-Assadi, A. A.; Sbeih, S.; Dunbar, P. G.;Roknich, S.; Rho,T.; Fang, Z.; Ojo, B.; Zhang, H.; Huzl III, J. J.; Nagy, P. I. J. Med. Chem. 1997, 40, 1230-1246; Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.; Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.; Wadsworth, H. J.; Wyman, P. J. Med. Chem. 1991, 34, 2726-2735.
2. Messer Jr., W. S.; Abuh, Y. F.; Liu, Y; Periyasamy, S.; Ngur, D. O.; Edgar, M. A. N.; El-Assadi, A. A.; Sbeih, S.; Dunbar, P. G.;Roknich, S.; Rho,T.; Fang, Z.; Ojo, B.; Zhang, H.; Huzl III, J. J.; Nagy, P. I. J. Med. Chem. 1997, 40, 1230-1246; Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.; Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.; Wadsworth, H. J.; Wyman, P. J. Med. Chem. 1991, 34, 2726-2735.
3. Watjen, F.; Baker, R.; Engelstoff, M.; Herbert, R.; MacLeod, A.; Knight, A.; Merchant, K.; Moseley, J.; Saunders, J.; Swain, C. J.; Wong, E.; Springer, J. P. J. Med. Chem. 1989, 32, 2282-2291.
4. Clitherow, J. W.; Beswick, P.; Irving, W. J.; Scopes, D. I. C; Barnes, J. C; Clapham, J.; Brown, J. D.; Evans, D. J.; Hayes, A. G. Bioorg. Med. Chem. Lett. 1996, 6, 833-838.
5. Diana, G. D.; Volkots, D. L.; Nitz, T. J.; Bailey, T. R.; Long, M. A.; Vescio, N.; Aldous, S.; Pevear, D. C.; Dutko, F. J. J. Med Chem. 1994, 37, 2421-2436.
6. Andersen, K. E.; Lundt, B. F.; Joergensen, A. S.; Braestrup, C. Eur. J. Med. Chem. 1996, 31, 417-425.
7. Chiou, S.; Shine, H. J. J. Met. Chem. 1989, 26, 125-128.
8. Liang, G.-B.; Feng, D. D. Tetrahedron Lett. 1996,37, 6627-6630.
9. Deegan, T. L.; Nitz, T. J.; Cebzanov, D.; Pufko, D. E.; Porco Jr., J. A. Bioorg. Med. Chem. Lett. 1999, 9,209-212.
10. Young, J. R.; DeVita, R. J. Tetrahedron Lett. 1998, 39, 3931-3934.
11. Ngu, K.; Patel, D. V. Tetrahedron Lett. 1997, 38, 973-976.
12. Katritzky, A. R.; Toader, D.; Watson, K.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 7849-7850.
13. New products were characterized by HPLC-MS after cleavage from the resin using TFA or HF. Examples: Boc-Ala, Boc-5-aminocaproic acid, Boc-Arg(Tos), Boc-Asp-(OcHex), Boc-cyclohexylalanine, Boc-Glu-(OcHex), Boc-Gly, Boc- His(Tos), Boc-Ile, Boc-isonipecotic acid, Boc-Leu, Boc-Nipecotic Acid, Boc-Phe, Boc-D,L-pipecolinic acid, Boc-Pro, Boc-Ser(OBn), Boc-Thr(OBn), Boc-TIC, Boc-Trp(For), Boc-Tyr(OBn), Boc-Val, W-Fmoc-Lys(Boc).
14. +).