Excellent acceleration of the Diels-Alder reaction by microwave irradiation for the synthesis of new fluorine-substituted ligands of NMDA receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 21, 1998, Pages 2983-2986

  Sasaki, Shigeki ^a   Ishibashi, Nobuyasu ^a   Kuwamura, Tshuneo ^a   Sano, Hiromi ^a   Matoba, Masaki ^b   Nisikawa, Tohru ^b   Maeda, Minora ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF NEUROSCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

N METHYL DEXTRO ASPARTIC ACID RECEPTOR; QUINOLIZINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; MICROWAVE IRRADIATION;

ANIMALS; FLUORINE RADIOISOTOPES; LIGANDS; MICROWAVES; RATS; RECEPTORS, N-METHYL-D-ASPARTATE;

BETULACEAE;

EID: 0032211603     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00541-1     Document Type: Article

References (11)

1. 1) Collingridge, G. L. and Watkins, J. C. ed., "The NMDA Receptor" 2nd Ed., Oxford University Press, New York, 1994.
2. 2) a) Blin, J.; Denis, A.; Yamaguchi, T.; Crouzel, C.; MacKenzie, E. T.; Baron, J. C. Neuroscience Letters. 121, 183-186, (1991),
3. b) Orita, K.; Sasaki, S.; Maeda, M.; Hashimoto, A.; Nishikawa, T.; Yugami, T.; Umezu, K., Nucl. Med. Biol. 20, 865-873, (1993), and references cited therein.
4. 3) Mallamo, J. P.; Earley, W. G.; Kumar, V.; Subramanyam, C.; Dority, Jr. J. A.; Miller, M. S.; DeHaven-Hudkins, D. L.; Ault, B.; Herrmann, Jr. J. L.; Dung, J.-S.; McMullen, L. A.; Jaeger, E.; Kullnig, R.; Magee, L. J. J. Med. Chem. 37, 4438-4448, (1994).
5. 4) Shibayama, Y.; Sasaki, S.; Tomita, U.; Maeda, M. J. Label. Compds. Radiopharm. 38, 77-86, (1996).
6. 5) A similar solvent effect was reported, van der Wel, G. K.; Wijnen, J. W. and Engberts, J. B. F. N. J. Org. Chem. 61, 9001-9005 (1996), and reference cited therein.
7. 6) Recent reviews on microwave irradiation: Sridar, V. Current Science, 74, 446-450 (1998), Caddick S. Tetrahedron, 51, 10403-10432 (1995).
8. 6) Recent reviews on microwave irradiation: Sridar, V. Current Science, 74, 446-450 (1998), Caddick S. Tetrahedron, 51, 10403-10432 (1995).
9. 18F]18 and 19 in 20% radiochemical yield in 1:1 ratio at the synthesis time of 77 min including HPLC purification.
10. 1H-NMR, IR as well as high resolution FAB mass spectra.
11. 9) 17 was synthesized by the following scheme. (metric presented)