Immobilized triazine-type dehydrocondensing reagents for carboxamide formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 5, 2007, Pages 825-828

  Hioki, Kazuhito ^a   Kameyama, Satomi ^a   Tani, Shohei ^a   Kunishima, Munetaka ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

Amide; Dehydrocondensation; Immobilized reagent; Ring opening metathesis polymerization (ROMP); Triazine

Indexed keywords

AMIDINE; CARBOXYLIC ACID; POLYMER; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROPHILICITY; MOLECULAR WEIGHT; RING OPENING METATHESIS POLYMERIZATION;

INDICATORS AND REAGENTS; POLYMERS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; TRIAZINES;

EID: 34248141101     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.825     Document Type: Article

References (39)

1. Uozumi Y., Yamada Y., Kagaku Furontia, 16, 155-163 (2006).
2. Parlow J. J., Curr. Opin. Drug Discovery Dev., 8, 757-775 (2005).
3. Gonthier E., Breinbauer R., Molecular Diversity, 9, 51-62 (2005).
4. Harned A. M., Zhang M., Vedantham P., Mukherjee S., Herpel R. H., Flynn D. L., Hanson P. R., Aldrichimica Acta, 38, 3-16 (2005).
5. Katritzky A. R., Suzuki K., Singh S. K., ARKIVOC, i, 12-35 (2004).
6. Barrett A. G. M., Hopkins B. T., Köbberling J., Chem. Rev., 102, 3301-3324 (2002). See also references therein.
7. Kirschning A., Monenschein H., Wittenberg R., Angew. Chem. Int. Ed., 40, 650-679 (2001).
8. Ley S. V., Baxendale I. R., Bream R. N., Jackson P. S., Leach A. G., Longbottom D. A., Nesi M., Scott J. S., Storer R. I., Taylor S. J., J. Chem. Soc., Perkin Trans. 1, 2000, 3815-4195 (2000).
9. Thompson L. A., Curr. Opin. Chem. Biol., 4, 324-337 (2000).
10. Valeur E., Bradley M., Chem. Commun., 2005, 1164-1166 (2005).
11. Barrett A. G. M., Bibal B., Hopkins B. T., Köbberling J., Love A. C., Tedeschi L., Tetrahedron, 61, 12033-12041 (2005).
12. Filip S. V., Lejeune V., Vors J.-P., Martinez J., Cavelier F., Eur. J. Org. Chem., 2004, 1936-1939 (2004).
13. Donati D., Morelli C., Porcheddu A., Taddei M., J. Org. Chem., 69, 9316-9318 (2004).
14. Crosignani S., Gonzalez J., Swinnen D., Org. Lett., 6, 4579-4582 (2004).
15. Chinchilla R., Dodsworth D. J., Nájera C., Soriano J. M., Yus M., ARKIVOC, x, 41-47 (2003).
16. Disadee W., Watanabe T., Ishikawa T., Synlett, 2003, 115-117 (2003).
17. Desai M. C., Stramiello L. M. S., Tetrahedron Lett., 34, 7685-7688 (1993).
18. Kaminski Z. J., Biopolymers, 55, 140-164 (2000).
19. Kunishima M., Yamamoto K., Watanabe Y., Hioki K., Tani S., Chem. Commun., 2005, 2698-2700 (2005).
20. Hioki K., Yamamoto K., Tani S., Kunishima M., "Peptide Science 2005," ed by Wakamiya T., The Japanese Peptide Society, Osaka, 2006, pp. 485-486.
21. Kunishima M., Kawachi C., Iwasaki F., Terao K., Tani S., Tetrahedron Lett., 40, 5327-5330 (1999).
22. Kunishima M., Kawachi C., Morita J., Terao K., Iwasaki F., Tani S., Tetrahedron, 55, 13159-13170 (1999).
23. Kunishima M., Kawachi C., Hioki K., Terao K., Tani S., Tetrahedron, 57, 1551-1558 (2001).
24. Kunishima M., Kitao A., Kawachi C., Watanabe Y., Iguchi S., Hioki K., Tani S., Chem. Pharm. Bull., 50, 549-550 (2002).
25. Falchi A., Giacomelli G., Porcheddu A., Taddei M., Synlett, 2000, 275-277 (2000).
26. Armitt D. J., Aust. J. Chem., 54, 469 (2001).
27. Fu G. C., Nguyen S. T., Grubbs R. H., J. Am. Chem. Soc., 115, 9856-9857 (1993).
28. Schwab P., France M. B., Ziller J. W., Grubbs R. H., Angew. Chem. Int. Ed., 34, 2039-2041 (1995).
29. Scholl M., Ding S., Lee C. W., Grubbs R. H., Org. Lett., 1, 953-956 (1999).
30. Trnka T. M., Grubbs R. H., Acc. Chem. Res., 34, 18-29 (2001), and references cited therein.
31. Grubbs R. H., Sanford M., Mathematics, Physics and Chemistry, 56, 17-21 (2002).
32. Fuchter M. J., Hoffman B. M., Barrett A. G. M., J. Org. Chem., 71, 724-729 (2006).
33. Barrett A. G. M., Hopkins B. T., Love A. C., Tedeschi L., Org. Lett., 6, 835-837 (2004).
34. Årstad E., Barrett A. G. M., Tedeschi L., Tetrahedron Lett., 44, 2703-2707 (2003).
35. Stille J. K., Frey D. A., J. Am. Chem. Soc., 81, 4273-4275 (1959).
36. 50-Cl in MeOH, the yield of amide decreased to 67% presumably due to ineffi-cient heterogeneous conditions.
37. The epimerizatoin test was performed by HPLC analysis according to ref. 23.
38. Kunishima M., Hioki K., Wada A., Kobayashi H., Tani S., Tetrahedron Lett., 43, 3323-3326 (2002).
39. Dudley J. R., Thurston J. T., Schaefer F. C., Holm-Hansen D., Hull C. J., Adams P., J. Am. Chem. Soc., 73, 2986-2990 (1951).