Broadening the scope of 1,2,4-triazine synthesis by the application of microwave technology

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1123-1127

  Zhao, Zhijian ^a   Leister, William H ^a   Strauss, Kimberly A ^a   Wisnoski, David D ^a   Lindsley, Craig W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZINE DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CLINICAL PROTOCOL; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE RADIATION; SYNTHESIS; TECHNOLOGY;

EID: 0037415505     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02845-9     Document Type: Article

References (24)

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2. For an excellent review, see: (a) Boger, D. L. Chem Rev. 1986, 86, 781; (b) Benson, S. C.; Li, J.-H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285.
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8. (a) Robinson, L.; Vanderwala, P. H.; Laakso, P. V. Tetrahedron 1957, 1, 103; (b) Metze, R. Chem Ber. 1955, 88, 772; © Metze, R. Chem Ber. 1954, 87, 1540; (d) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1977, 33, 1043; For excellent reviews, see: (e) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines; Wiley-Interscience: New York, 1978; pp. 194-200; (f) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W.; Boulton, A. J.; McKilop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 385-456.
9. (a) Robinson, L.; Vanderwala, P. H.; Laakso, P. V. Tetrahedron 1957, 1, 103; (b) Metze, R. Chem Ber. 1955, 88, 772; © Metze, R. Chem Ber. 1954, 87, 1540; (d) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1977, 33, 1043; For excellent reviews, see: (e) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines; Wiley-Interscience: New York, 1978; pp. 194-200; (f) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W.; Boulton, A. J.; McKilop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 385-456.
10. (a) Robinson, L.; Vanderwala, P. H.; Laakso, P. V. Tetrahedron 1957, 1, 103; (b) Metze, R. Chem Ber. 1955, 88, 772; © Metze, R. Chem Ber. 1954, 87, 1540; (d) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1977, 33, 1043; For excellent reviews, see: (e) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines; Wiley-Interscience: New York, 1978; pp. 194-200; (f) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W.; Boulton, A. J.; McKilop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 385-456.
11. (a) Robinson, L.; Vanderwala, P. H.; Laakso, P. V. Tetrahedron 1957, 1, 103; (b) Metze, R. Chem Ber. 1955, 88, 772; © Metze, R. Chem Ber. 1954, 87, 1540; (d) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1977, 33, 1043; For excellent reviews, see: (e) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines; Wiley-Interscience: New York, 1978; pp. 194-200; (f) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W.; Boulton, A. J.; McKilop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 385-456.
12. (a) Robinson, L.; Vanderwala, P. H.; Laakso, P. V. Tetrahedron 1957, 1, 103; (b) Metze, R. Chem Ber. 1955, 88, 772; © Metze, R. Chem Ber. 1954, 87, 1540; (d) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1977, 33, 1043; For excellent reviews, see: (e) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines; Wiley-Interscience: New York, 1978; pp. 194-200; (f) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W.; Boulton, A. J.; McKilop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 385-456.
13. Taylor E.C., French L.G. J. Org. Chem. 54:1989;1245. and references cited therein.
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16. Kidwai M. Pure Appl. Chem. 73:2001;147.
17. Due to vague experimental procedures in Ref. 4b, repeating the published work proved difficult. However, attempts to optimize reaction variables in the Smithsynthesizer™, in place of a conventional microwave oven, afforded very poor results with 'dry media'.
18. For a review with accounts of heterocycles synthesized by microwave heating, see: Lidstrom P., Tierney J., Wathey B., Westman J. Tetrahedron. 57:2001;925.
19. For information on Personal Chemistry's microwave technology for organic synthesis, see: http:\\www.personalchemistry.com.
20. 5(M+H), 300.1244; found 300.1248 (M+H).
21. Leister, W. H.; Strauss, K. A.; Wisnoski, D. D.; Zhao, Z.; Lindsley, C. W. J. Comb. Chem., submitted.
22. 4S (M+H), 317.0857; found 317.0856 (M+H).
23. Searches of CAS, SciFinder and Bielstein indicated that these compounds are new chemical entities, unknown in the primary and/or patent literature.
24. 4O (M+H), 267.1241; found 267.1242 (M+H).