Direct conversion of 4-amino-2-phenyl-2-oxazolines into either 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides

Tetrahedron Letters

Volumn 44, Issue 19, 2003, Pages 3809-3812

  Guirado, Antonio ^a   Andreu, Raquel ^a   Gálvez, Jesús ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Oxazolidines; Oxazolines; Thiazolidines; Thioureas; Ureas

Indexed keywords

HYDROCHLORIC ACID; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; OXAZOLIDINE DERIVATIVE; OXAZOLINE DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; SYNTHESIS;

EID: 0037420782     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00783-4     Document Type: Article

References (18)

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4. Unpublished results.
5. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
6. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
7. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
8. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
9. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
10. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
11. For reviews, see: (a) Wiley, R. H.; Bennett, L. L. Chem. Rev. 1949, 44, 447; (b) Seeliger, W.; Aufderhaar, E.; Diepers, W.; Feinauer, R.; Nehring, R.; Their, W.; Hellmann, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 875; (c) Frump, J. A. Chem. Rev. 1971, 71, 483; (d) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 15, 270; (e) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837; (f) Maryanoff, B. E. In Chemistry of Heterocyclic Compounds; Turchi, I., Ed. Oxazoles. John Wiley & Sons: Chichester, 1986; Vol. 45, p. 963; (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
12. 1H NMR spectra for crude and crystalline products were recorded showing negligible differences.
13. -1.
14. Details of the structure determination will be reported in a future full paper.
15. Guirado, A.; Andreu, R.; Cerezo, A.; Gálvez, J. Tetrahedron 2001, 39, 4925.
16. See for example: Ciba-Geigy Corporation (1993), US Patent 5,229,405; Egls Gyogyszergyar (1987), US Patent 4,665,083; ICI Americas Inc. (1989), US Patent 4,877,880; ICI Americas Inc. (1990), US Patent 4,900,351; ICI Americas Inc. (1993), US Patent 5,266,701; Union Carbide Corporation (1985), US Patent 4,525,357.
17. Challis, B. C.; Challis, J. A. In Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 2 (Sutherland, O. I., Ed.), p. 974 Andersen, K. K. In Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3 (Jones, D. N., Ed.), p. 456.
18. Whitham G.H. Organosulfur Chemistry. 1995;26 Oxford University Press, Oxford.