Development of novel polymer-type dehydrocondensing reagents comprised of chlorotriazines

Chemical Communications

Volumn , Issue 21, 2005, Pages 2698-2700

  Kunishima, Munetaka ^a,b   Yamamoto, Kazuyoshi ^a   Watanabe, Yasunobu ^a   Hioki, Kazuhito ^a   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOXYLIC ACID; CHLOROTRIAZINE DERIVATIVE; ETHER DERIVATIVE; POLYMER; TETRA(ETHYLENE GLYCOL) BIS(DICHLOROTRIAZINYL)ETHER; TRIAZINE DERIVATIVE; TRIS(2 AMINOETHYL)AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; POLYMERIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 20744445824     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501917f     Document Type: Article

References (29)

1. (a) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. C. Scott, R. I. Storer and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815;
2. (b) A. Kirschning, H. Monenschein and R. Wittenberg, Angew. Chem. Int. Ed., 2001, 40, 650;
3. (c) C. C. Tzschucke, C. Markert, W. Bannwarth, S. Roller, A. Hebel and R. Haag, Angew. Chem. Int. Ed., 2002, 41, 3694;
4. (d) C. A. McNamara, M. J. Dixon and M. Bradley, Chem. Rev., 2002, 102, 3275.
5. (a) J. Brown and R. E. Williams, Can. J. Chem., 1971, 49, 3765;
6. (b) N. M. Weinshenker and C.-M. Shen, Tetrahedron Lett., 1972, 3285;
7. (c) N. M. Weinshenker, C.-M. Shen and J. Y. Wong, Org. Synth., 1988, Coll. Vol. VI, 951;
8. (d) R. Chinchilla, D. J. Dodsworth, C. Nájera and J. M. Soriano, Tetrahedron Lett., 2000, 41, 2463;
9. (e) W. Disadee, T. Watanabe and T. Ishikawa, Synlett, 2003, 115.
10. Abbreviations used in this report are as follows: DCC: 1,3-dicyclohexylcarbodiimide; EEDQ: 2-ethoxy-1-ethoxycarbonyl-1,2- dihydroquinoline; TBTU: N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene-N- methylmethanaminium tetrafluoroborate N-oxide; DMC: 1,3-dimethyl-2- imidazolidinone; EDC: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; MeO-PEiGOH: poly(ethylene glycol) monomethyl ether; DMT-MM: 4-(4,6-dimethoxy-1,3,5-triazin- 2-yl)-4-methylmorpholinium chloride; CDMT: 2-chloro-4,6-dimethoxy-1,3,5- triazine; NMM: N-methylmorpholine; HO-DMT: 2-hydroxy-4,6-dimethoxytriazine.
11. (a) M. C. Desai and L. M. S. Stramiello, Tetrahedron Lett., 1993, 34, 7685;
12. (b) M. Adamczyk and J. R. Fishpaugh, Tetrahedron Lett., 1996, 37, 7171;
13. (c) C. F. Sturino and M. Labelle, Tetrahedron Lett., 1998, 39, 5891.
14. Catalytic decarbonylation of highly toxic diisocyanatohexane is known to give hexamethylenecarbodiimide with a linear polymeric structure, which would be hardly utilized. Y. Wolman, S. Kivity and M. Frankel, Chem. Commun., 1967, 629.
15. (a) M. Kunishima, C. Kawachi, F. Twasaki, K. Terao and S. Tani, Tetrahedron Lett., 1999, 40, 5327;
16. (b) M. Kunishima, C. Kawachi, J. Monta, K. Terao and S. Tani, Tetrahedron, 1999, 55, 13159;
17. (c) M. Kunishima, C. Kawachi, K. Hioki, K. Terao, F. Iwasaki and S. Tani, Tetrahedron, 2001, 57, 1551.
18. Z. J. Kaminski, Biopolymers, 2000, 55, 140.
19. (a) S. Masala and M. Taddei, Org. Lett., 1999, 9, 1355;
20. (b) G. Luo, L. Xu and G. S. Poindexter, Tetrahedron Lett., 2002, 43, 8909.
21. A. Falchi and M. Taddei, Org. Lett., 2000, 22, 3429.
22. 11 the polymers of this type used as a dehydrocondensing reagent have not been reported, to the best of our knowledge.
23. (a) G. Allen and A. G. De Boos, Polymer, 1974, 15, 56;
24. (b) Y. Oishi, Kobunshi, 1999, 48, 274.
25. P. de Hoog, P. Gamez, W. L. Driessen and J. Reedijk, Tetrahedron Lett., 2002, 43, 6783.
26. The yield was determined based on the theoretical structure of polymer A as illustrated in Scheme 1.
27. 3. See ESI.
28. ac, 4-(4-ethylamino-6-methoxy-1,3,5-triazin-2-yl)- 4-methylmorpholinium chloride (AMT-MM), which was prepared from 4-chloro-2-ethylamino-6-methoxy-1,3,5-triazine (AMT) by treatment with NMM.
29. M. Kunishima, K. Hioki, A. Wada, H. Kobayashi and S. Tani, Tetrahedron Lett., 2002, 43, 3323.