Synthesis and characterization of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)- 4-methylmorpholinium chloride

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5327-5330

  Kunishima, Munetaka ^a   Kawachi, Chiho ^a   Iwasaki, Fumiaki ^b   Terao, Keiji ^c   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b TOKUYAMA CORPORATION   (Japan)

^c Wacker Chemicals East Asia Ltd   (Japan)

Author keywords

Amides; Carboxylic acids and derivatives; Condensations; Triazines

Indexed keywords

AMINE; CARBOXYLIC ACID; CHLORIDE; MORPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS;

EID: 0033575461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00968-5     Document Type: Article

References (17)

1. (a) Kaminski, Z. J. Tetrahedron Lett. 1985, 26, 2901-2904. (b) Kaminski, Z. J. Synthesis 1987, 917-920.
2. (a) Kaminski, Z. J. Tetrahedron Lett. 1985, 26, 2901-2904. (b) Kaminski, Z. J. Synthesis 1987, 917-920.
3. For recent paper using CDMT: (a) Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599-1603. (b) Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991. (d) Kuciauskas, D.; Liddell, P. A.; Hung, S.-C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440. (e) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 1339-1349.
4. For recent paper using CDMT: (a) Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599-1603. (b) Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991. (d) Kuciauskas, D.; Liddell, P. A.; Hung, S.-C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440. (e) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 1339-1349.
5. For recent paper using CDMT: (a) Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599-1603. (b) Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991. (d) Kuciauskas, D.; Liddell, P. A.; Hung, S.-C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440. (e) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 1339-1349.
6. For recent paper using CDMT: (a) Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599-1603. (b) Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991. (d) Kuciauskas, D.; Liddell, P. A.; Hung, S.-C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440. (e) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 1339-1349.
7. For recent paper using CDMT: (a) Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599-1603. (b) Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193. (c) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991. (d) Kuciauskas, D.; Liddell, P. A.; Hung, S.-C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440. (e) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 1339-1349.
8. Unpublished result.
9. After we developed our method for the preparation and utilization of DMTMM that we reported here, a paper appeared describing the synthesis and characterization of DMTMM by Kaminski et al; see ref. 5.
10. Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248-4255.
11. 3 or DMSO at room temperature.
12. +) 226.1066, found 226.1072. The structure of DMTM was confirmed by comparison with the compounds obtained from CDMT and morpholine.
13. Jones, A. J.; Beeman, C. P.; Hasan, M. U.; Casy, A. F.; Hassan, M. M. A. Can J. Chem. 1976, 54, 126-135.
14. Kaminski, Z. J.; Paneth, P.; O'Leary, M. H. J. Org. Chem. 1991, 56, 5716-5718. Kaminski, Z. J. Int. J. Peptide Protein Res. 1994, 43, 312-319.
15. Kaminski, Z. J.; Paneth, P.; O'Leary, M. H. J. Org. Chem. 1991, 56, 5716-5718. Kaminski, Z. J. Int. J. Peptide Protein Res. 1994, 43, 312-319.
16. This consideration is also applicable to an acid anhydride, an alternative intermediate, arising from 4 and an acid.
17. Cronin, J. S.; Ginah, F. O.; Murray, A. R.; Copp, J. D. Synth. Commun. 1996, 26, 3491-3494. CDMT is commercially available.