From α,α-disubstituted α-aminonitriles to heterocycles: Synthesis of derivatives of 4-amino-29-dihydroisothiazole 1,1-dioxide, a new heterocyclic ring system

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4835-4836

  Marco, José L ^a   Ingate, Simon ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030958797     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01002-2     Document Type: Article

References (20)

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2. (b) Marco, J. L. J. Chem. Res. (S) 1988, 51;
3. (c) Marco, J. L.; Royer, J.; Husson. H.-P. Synth. Commun. 1987, 17, 669;
4. (d) Marco, J. L. J. Heterocyclic Chem. 1987, 24, 1235;
5. (e) Marco, J. L.; Royer, J.; Husson. H.-P. Tetrahedron Lett. 1985, 26, 6345;
6. (f) Marco, J. L.; Royer, J.; Husson. H.-P. Tetrahedron Lett. 1985, 26, 3567.
7. (a) Albright, J. D. Tetrahedron 1983, 39, 3207;
8. (b) Stork, G.; Ozorio, A. A.; Leong, A. Y. W. Tetrahedron Lett. 1978, 5175.
9. Stout, D. S.; Black, L. A.; Matier, W. L. J. Org. Chem. 1983, 48, 5369.
10. Williams, R. M. Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford 1989; Chapter V, pp 208-229.
11. Poupaert, J.; Bruylants, A.; Crooy, P. Synthesis 1972, 622, for the only example described about the synthesis of 1,3-oxazoles using acylamino derivatives of α-aminonitriles derived from aldehydes.
12. Calvo-Mateo, A.; Camarasa, M.-J.; Díaz-Ortìz, A.; De las Heras, F. G. Chem. Commun. 1988, 1114.
13. Pérez-Pérez, M. J.; Balzarini, J.; Hosoya, M.; De Clercq, E.; Camarasa, M.-J. BioMed. Chem. Lett. 1992, 2, 647.
14. Camarasa, M. J.; Pérez-Pérez, M. J.; San Félix, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721.
15. Camarasa, M.-J., personal communication.
16. α-Substituted N-(α-cyanoalkyl)sulphonamides are well known intermediates for the synthesis of useful molecules: Katritzky, A. R.; Oniciu, D. C.; Ghiviriga, I. Synth. Commun. 1997, 27, 907, and references cited therein.
17. Moore, J. E.; Yang, Y.-L.; Griffith, R. K.; Chan, D. Ch.-K. Eur. Pat. Appl. 0 176 327 A1. See also: Gulewitsch, W.; Wasmus, T. Chem. Ber. 1905, 39, 1181.
18. Moore, J. E.; Yang, Y.-L.; Griffith, R. K.; Chan, D. Ch.-K. Eur. Pat. Appl. 0 176 327 A1. See also: Gulewitsch, W.; Wasmus, T. Chem. Ber. 1905, 39, 1181.
19. All new compounds showed good spectroscopic and analytical data.
20. 3).