Solid phase synthesis of cyanoacetamidines: Fast access to potential bioisosteres of acceptor-substituted guanidines

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7291-7294

  Zaragoza, Florencio ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030722306     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01694-8     Document Type: Article

References (23)

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11. Recent reviews: Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472; Balkenhohl, F.; Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; Früchtel, J. S.; Jung, G. ibid. 1996, 108, 19-46 and 1996, 35, 17-42.
12. Recent reviews: Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472; Balkenhohl, F.; Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; Früchtel, J. S.; Jung, G. ibid. 1996, 108, 19-46 and 1996, 35, 17-42.
13. Durant, G. J.; Emmett, J. C.; Ganellin, C. R.; Prain H. D. (Smith Kline and French Laboratories Ltd.), US Patent 4277485, 1981 [Chem. Abstr. 1981, 95, 156591r]; idem, CH Patent 606026, 1978 [Chem. Abstr. 1979, 90, 87449h].
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15. Klemm, K.; Prüsse, W.; Baron, L.; Daltrozzo, E. Chem. Ber. 1981, 114, 2001-2018; Clark, J.; Parvizi, B.; Southon, I. W. J. Chem. Soc., Perkin Trans. 1 1976, 125-130; Hashimoto, N.; Kawano, Y.; Morita, K. J. Org. Chem. 1970, 35, 828-831; Fanshawe, W. J.; Bauer, V. J.; Ullman, E. F.; Safir, S. R. J. Org. Chem. 1964, 29, 308-311.
16. Klemm, K.; Prüsse, W.; Baron, L.; Daltrozzo, E. Chem. Ber. 1981, 114, 2001-2018; Clark, J.; Parvizi, B.; Southon, I. W. J. Chem. Soc., Perkin Trans. 1 1976, 125-130; Hashimoto, N.; Kawano, Y.; Morita, K. J. Org. Chem. 1970, 35, 828-831; Fanshawe, W. J.; Bauer, V. J.; Ullman, E. F.; Safir, S. R. J. Org. Chem. 1964, 29, 308-311.
17. Klemm, K.; Prüsse, W.; Baron, L.; Daltrozzo, E. Chem. Ber. 1981, 114, 2001-2018; Clark, J.; Parvizi, B.; Southon, I. W. J. Chem. Soc., Perkin Trans. 1 1976, 125-130; Hashimoto, N.; Kawano, Y.; Morita, K. J. Org. Chem. 1970, 35, 828-831; Fanshawe, W. J.; Bauer, V. J.; Ullman, E. F.; Safir, S. R. J. Org. Chem. 1964, 29, 308-311.
18. 3 (393.36): C, 58.01; H, 4.61; N, 10.68. Found: C, 57.98; H, 4.68; N, 10.47.
19. Zaragoza, F. Tetrahedron Lett. 1996, 37, 6213-6216.
20. This EDC-mediated condensation reaction also proceeds in solution (12-47% yield, Zaragoza, F.; unpublished results). Higher yields of ketene aminals were however obtained with mercury(II) oxide as desulfurizing agent. Peseke, K. Ger. (East) Patent 98914, 1973 [Chem. Abstr. 1974, 80, 59723t].
21. Atwal, K. S.; Ahmed, S. Z.; O'Reilly, B. C. Tetrahedron Lett. 1989, 30, 7313-7316. For a similar guanidine synthesis on solid support, see Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697-6705.
22. Atwal, K. S.; Ahmed, S. Z.; O'Reilly, B. C. Tetrahedron Lett. 1989, 30, 7313-7316. For a similar guanidine synthesis on solid support, see Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697-6705.
23. 13C NMR and HPLC (254 nm and 214 nm). The molecular formulas were confirmed either by elemental analysis or by high-resolution MS. We acknowledge Dr. D. Börder and Dr. G. Remberg (University of Göttingen, Germany) for the recording of HRMS spectra.