Cyclization of tautomeric 1,5-dinitrile systems with hydrogen halides: A definitive mechanistic rationalization?

Heterocycles

Volumn 50, Issue 2, 1999, Pages 739-756

  Teixidó, Jordi ^a   Borrell, José I ^a   Serra, Blanca ^a   Matallana, Josep Lluis ^a   Colominas, Carles ^a   Carrión, Francisco ^a   Pascual, Rosalia ^a   Falcó, Josep Lluis ^a   Batllori, Xavier ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DINITRILE; HALIDE; HYDROGEN HALIDE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; DIMERIZATION; REACTION ANALYSIS;

EID: 0033117734     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)70     Document Type: Article

References (21)

1. (a) F. Johnson and R. Madroñero, 'Advances in Heterocyclic Chemistry', Vol. 6, ed. by A. R. Katritzky, Academic Press Inc, New York, 1966, pp. 95-146.
2. (b) A. I. Meyers and J. C. Sircar, 'The Chemistry of the Cyano Group', ed. by Z. Rappoport, Interscience Publishers, London-New York, 1970, pp. 341-421.
3. (c) S. Yangida, M. Okahara, and S. Komori, 'Advances in Organic Chemistry', Vol. 9, part 2, ed. by H. Böhme and H. G. Viehe, John Wiley and Sons, New York, 1979, pp. 527-571.
4. C. Grundmann, G. Wiesse, and S. Seide, Ann., 1952, 577, 77.
5. Heating in acetic acid of the intermediate imino thioester caused the formation of a 3-amino-2-alkylthioisoquinoline in which the alkylthio group is beard by the carbon atom of the arylic nitrile present in 2-cyanobenzyl cyanide.
6. P. Victory, R. Nomen, O. Colomina, M. Garriga, and A. Crespo, Heterocycles, 1985, 23, 1135.
7. P. Victory and M. Garriga, Heterocycles, 1985, 23, 1947.
8. P. Victory and M. Garriga, Heterocycles, 1985, 23, 2853.
9. P. Victory and M. Garriga, Heterocycles, 1986, 24, 3053.
10. (a) P. Victory, J. Teixidó, and J. I. Borrell, Heterocycles, 1992, 34, 1905.
11. (b) P. Victory, J. Teixidó, J. I. Borrell, and N. Busquets, Heterocycles, 1993, 36, 1.
12. P. Victory, J. Cirujeda, and A. Vidal-Ferran, Tetrahedron, 1995, 51, 10253.
13. P. Victory, N. Busquets, J. I. Borrell, J. Teixidó, B. Serra, J. L. Matallana, H. Junek, and H. Sterk, Heterocycles. 1995, 41, 1013.
14. J. I. Borrell, J. Teixidó, B. Martínez-Teipel, B. Serra, J. L. Matallana, M. Costa, and X. Batllori, Coll. Czech. Chem. Commun., 1996, 61, 901.
15. (a) A. Gordon and A. R. Katritzky, Tetrahedron Lett., 1968, 2767.
16. (b) P. Cieplak, P. Bash, U. C. Singh, and A. P. Kollman, J. Am. Chem. Soc., 1987, 109, 6283.
17. P. Beak, F. S. Fry, J. Lee, and F. Steele, J. Am. Chem. Soc., 1976, 98, 171.
18. J. Teixidó, J. I. Borrell, B. Serra, C. Colominas, X. Batllori, J. F. Piniella, and A. Alvarez-Larena, Tetrahedron, 1997, 53, 4487.
19. R. Pascual, Master Thesis, Institut Químic de Sarrià, Universitat Ramon Llull, Barcelona, 1998.
20. B. Serra, Estudi del mecanisme de ciclació de sistemes 1,5-dinitrilics amb possibilitat de tautomeria. PhD Disertation, Universitat Ramon Llull, Barcelona, 1996.
21. C. Colominas, M. Orozco, F. J. Luque, J. I. Borrell, and J. Teixidó, J. Org. Chem., 1998, 63, 4947.