Hetero-1,3-dipolar cycloadditions of dithiolane-isocyanate imminium methylides: A novel route to 1,3-oxazolidine- and thiazolidine-2-thiones

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 711-714

  Fishwick, Colin W G ^a   Foster, Richard J ^a   Carr, Robin E ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0030049903     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02249-X     Document Type: Article

References (15)

1. Fishwick, C.W.G.; Foster, R.J.; Carr, R.E. Tetrahedron Lett. 1995, in press.
2. Prepared by addition of an equivalent of trimethylsilylmethyltrifluoromethanesulphonate to N-methyl 1,3-dithiolane, For a synthesis of N-methyl 1,3-dithiolane, see: Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Japan 1970, 43, 162.
3. Huisgen, R. Angew. Chem. Int. Ed. Engl. 1963, 2, 565.
4. Cycloaddition of azomethine ylides across several classes of heterodipolarophile are known, see: Lown, J.W. in 1,3-Dipolar Cycloaddition Chemistry; Ed. Padwa, A.; Wiley, Vol. 1, p. 653 and references therein.
5. A C=O double bond is the most common trapping agent, for some more recent examples see: (a) Kohra, S.; Ueda, K.; Tominaga, Y.; Chem. Pharm. Bull. 1995, 43, 204.
6. (b) Tominaga, Y.; Takada, S.; Kohra, S. Heterocycles 1995, 105.
7. (c) Tominaga, Y.; Ogata, K.; Kohra, S.; Hojo, M.; Hosomi, A. Tetrahedron Lett. 1991, 32, 5987.
8. (d) Tominaga, Y.; Yanagai, T.; Hojo, M.; Miyashiro, Y.; Hosomi, A. J. Org. Chem. 1990, 55, 5308.
9. (e) Padwa, A.; Haffmans, G.; Tomas, M. J. Org. Chem. 1984, 49, 3314.
10. On attempted cycloaddition to simple non-conjugated aldehydes and ketones (eg. acetone, cyclohexanone and butyraldehyde), no reaction was observed.
11. Decomposition of similar 1,4,5,9-hetero spiro[4.4]nonanes has been observed, see: (a) Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Japan 1970, 43, 168.
12. (b) Baba, A.; Yano, K.; Amishiro, N.; Matsuda, H. Bull. Chem. Soc. Japan 1991, 64, 2661.
13. 2 requires(%) C 56.92 H 5.93 N 5.53 found(%) C 56.60 H 5.60 N 5.40. Complete experimental details will be published elsewhere.
14. Lawesson, S.O.; Scheibye. S.; Shabana, R. Tetrahedron 1982, 38, 993.
15. Fleming, I. in Frontier Orbitals and Organic Chemical Reactions; Wiley, 1976, pp. 148-160.