Reverse-cope cyclisations of thiahydroxylamines derived from the addition of allylic thiols to nitrones: Syntheses of 1,3-thiazolidine-N-oxides and 1,5,2-oxathiazinanes

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8549-8552

  Coogan, Michael P ^a   Gravestock, Michael B ^b   Knight, David W ^a   Thornton, Steven R ^c  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLIDINE DERIVATIVE;

AMINATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030693920     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10244-1     Document Type: Article

References (18)

1. Bell, K.E.; Coogan, M.P.; Gravestock, M.B.; Knight, D.W.; Thornton, S.R. Tetrahedron Lett., 1997, 38, 8545; Gravestock, M.B.; Knight, D.W.; Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169.
2. Bell, K.E.; Coogan, M.P.; Gravestock, M.B.; Knight, D.W.; Thornton, S.R. Tetrahedron Lett., 1997, 38, 8545; Gravestock, M.B.; Knight, D.W.; Thornton, S.R. J. Chem. Soc., Chem. Commun., 1993, 169.
3. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
4. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
5. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
6. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
7. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
8. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
9. House, H.O.; Manning, D.T.; Melillo, D.G.; Lee, L.F.; Haynes, O.R.; Wilkes, B.E. J. Org. Chem., 1976, 41, 855; Black, D.StC.; Doyle, J.E. Aust. J. Chem., 1978, 31, 2317; Oppolzer, W.; Siles, S.; Snowden, R.L.; Bakker, B.H.; Petrzilka, M. Tetrahedron Lett., 1979, 4391; Oppolzer, W.; Spivey, A.C.; Bochet, C.G. J. Am. Chem. Soc., 1994, 116, 3139; Ciganek, E. J. Org. Chem., 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795; Davison, E.C.; Forbes, I.T.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601, and references cited therein.
10. For a review of N-oxide chemistry, see Albini A. Synthesis, 1993, 263.
11. Hacklert, R.E.; Balko, T.W. J. Org. Chem., 1973, 38, 2106. It was fortunate that this thiol reacted at ambient temperature as heating causes rapid rearrangement to the corresponding cinnamylthiol.
12. Dondoni, A; Merino, P. Comp. Heterocyclic Chem., II, Eds. Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V. Elsevier Science Ltd., Oxford, 1996, 3, 402.
13. We are very grateful to Professor M.B. Hursthouse and Mr D.E. Hibbs, Cardiff University, for these data, full details of which will be reported separately.
14. At ambient temperature in chloroform, the thiazolidine-N-oxide 9a slowly (>15 days) underwent Meisenheimer rearrangement to the oxathiazinane 14 but this was accompanied by similar amounts of the two possible S-oxides derived from these ring systems, presumably formed by N-to S-oxygen transfer.
15. Yoshimura, T.; Asada, K.; Oae, S. Bull. Chem. Soc. Japan, 1982, 55, 3000 and references therein.
16. 4H-1,5,2-Oxathiazines have been obtained from Diels-Alder cycloadditions of conjugated nitrosoalkenes with thioketones : Bonini, B.F.; Foresti, E.; Maccagnati, G.; Mazzanti, G.; Sabatino, P.; Zani, P. Tetrahedron Lett., 1985, 26, 2131; Ascherl, B.; Kresze, G.; Vaerman, J.L.; Vandenbulck-Coyette, B.; Viehe, H.G. Bull. Chem. Soc. Belges, 1987, 96, 51. See also Ishida, M.; Ichikawa, K.; Asano, M.; Nakanishi, H.; Kato, S. Synthesis, 1987, 349.
17. 4H-1,5,2-Oxathiazines have been obtained from Diels-Alder cycloadditions of conjugated nitrosoalkenes with thioketones : Bonini, B.F.; Foresti, E.; Maccagnati, G.; Mazzanti, G.; Sabatino, P.; Zani, P. Tetrahedron Lett., 1985, 26, 2131; Ascherl, B.; Kresze, G.; Vaerman, J.L.; Vandenbulck-Coyette, B.; Viehe, H.G. Bull. Chem. Soc. Belges, 1987, 96, 51. See also Ishida, M.; Ichikawa, K.; Asano, M.; Nakanishi, H.; Kato, S. Synthesis, 1987, 349.
18. 4H-1,5,2-Oxathiazines have been obtained from Diels-Alder cycloadditions of conjugated nitrosoalkenes with thioketones : Bonini, B.F.; Foresti, E.; Maccagnati, G.; Mazzanti, G.; Sabatino, P.; Zani, P. Tetrahedron Lett., 1985, 26, 2131; Ascherl, B.; Kresze, G.; Vaerman, J.L.; Vandenbulck-Coyette, B.; Viehe, H.G. Bull. Chem. Soc. Belges, 1987, 96, 51. See also Ishida, M.; Ichikawa, K.; Asano, M.; Nakanishi, H.; Kato, S. Synthesis, 1987, 349.