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Volumn 68, Issue 11, 2003, Pages 4406-4409

Stereoselective synthesis of tetrasubstituted 2,3-dihydrofurans by one-step cyclization of β-ketosulfides of benzothiazole and aldehydes in ionic liquids

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 0038102404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026849a     Document Type: Article
Times cited : (43)

References (49)
  • 1
    • 77957077490 scopus 로고
    • Katritzky, A. R., Ed.; Academic: New York
    • (a) Dean, F. M. Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1982; Vol. 30, pp 167-238.
    • (1982) Advances in Heterocyclic Chemistry , vol.30 , pp. 167-238
    • Dean, F.M.1
  • 2
    • 84943382356 scopus 로고
    • Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon: New York
    • (b) Dean, F. M.; Sargent, M. V. Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon: New York, 1984; Vol. 4, Part 3, pp 531-598.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , Issue.PART 3 , pp. 531-598
    • Dean, F.M.1    Sargent, M.V.2
  • 13
    • 0038052385 scopus 로고    scopus 로고
    • (b) For a more detailed description about synthetic transformations of 2,3-dihydrofurans, see http://www.hwsands.com/snapshotpgs/chem23dh.htm.
  • 38
    • 0034721727 scopus 로고    scopus 로고
    • For further synthetic methods of dihydrofuran see also: (a) Dyker, G.; Thöne, A. Tetrahedron 2000, 56, 8669-8672. (b) Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821-1822. (c) Mélot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215-2224. (d) Boberg, F.; Garburg, K.-H., Görlich, K.-J.; Pipereit, E.; Redelfs, E.; Ruhr, M. J. Heterocycl. Chem. 1986, 23, 1853-1859. (e) Gianturco, M. A.; Friedel, P.; Flanagan, V. Tetrahedron Lett. 1965, (23), 1847-1852.
    • (2000) Tetrahedron , vol.56 , pp. 8669-8672
    • Dyker, G.1    Thöne, A.2
  • 39
    • 37049080860 scopus 로고
    • For further synthetic methods of dihydrofuran see also: (a) Dyker, G.; Thöne, A. Tetrahedron 2000, 56, 8669-8672. (b) Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821-1822. (c) Mélot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215-2224. (d) Boberg, F.; Garburg, K.-H., Görlich, K.-J.; Pipereit, E.; Redelfs, E.; Ruhr, M. J. Heterocycl. Chem. 1986, 23, 1853-1859. (e) Gianturco, M. A.; Friedel, P.; Flanagan, V. Tetrahedron Lett. 1965, (23), 1847-1852.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1821-1822
    • Mukherjee, A.K.1    Agosta, W.C.2
  • 40
    • 0001547271 scopus 로고
    • For further synthetic methods of dihydrofuran see also: (a) Dyker, G.; Thöne, A. Tetrahedron 2000, 56, 8669-8672. (b) Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821-1822. (c) Mélot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215-2224. (d) Boberg, F.; Garburg, K.-H., Görlich, K.-J.; Pipereit, E.; Redelfs, E.; Ruhr, M. J. Heterocycl. Chem. 1986, 23, 1853-1859. (e) Gianturco, M. A.; Friedel, P.; Flanagan, V. Tetrahedron Lett. 1965, (23), 1847-1852.
    • (1988) Tetrahedron , vol.44 , pp. 2215-2224
    • Mélot, J.M.1    Texier-Boullet, F.2    Foucaud, A.3
  • 41
    • 0038052383 scopus 로고
    • For further synthetic methods of dihydrofuran see also: (a) Dyker, G.; Thöne, A. Tetrahedron 2000, 56, 8669-8672. (b) Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821-1822. (c) Mélot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215-2224. (d) Boberg, F.; Garburg, K.-H., Görlich, K.-J.; Pipereit, E.; Redelfs, E.; Ruhr, M. J. Heterocycl. Chem. 1986, 23, 1853-1859. (e) Gianturco, M. A.; Friedel, P.; Flanagan, V. Tetrahedron Lett. 1965, (23), 1847-1852.
    • (1986) J. Heterocycl. Chem. , vol.23 , pp. 1853-1859
    • Boberg, F.1    Garburg, K.-H.2    Görlich, K.-J.3    Pipereit, E.4    Redelfs, E.5    Ruhr, M.6
  • 42
    • 0000389620 scopus 로고
    • For further synthetic methods of dihydrofuran see also: (a) Dyker, G.; Thöne, A. Tetrahedron 2000, 56, 8669-8672. (b) Mukherjee, A. K.; Agosta, W. C. J. Chem. Soc., Chem. Commun. 1994, 1821-1822. (c) Mélot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215-2224. (d) Boberg, F.; Garburg, K.-H., Görlich, K.-J.; Pipereit, E.; Redelfs, E.; Ruhr, M. J. Heterocycl. Chem. 1986, 23, 1853-1859. (e) Gianturco, M. A.; Friedel, P.; Flanagan, V. Tetrahedron Lett. 1965, (23), 1847-1852.
    • (1965) Tetrahedron Lett. , Issue.23 , pp. 1847-1852
    • Gianturco, M.A.1    Friedel, P.2    Flanagan, V.3
  • 44
    • 0038390709 scopus 로고    scopus 로고
    • note
    • Either α-chloroacetophenone or α-chloroacetone treated with benzaldehyde in the same reaction conditions did not afford any products.


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