Preparation of spiro hydroxy S-methylisothioureas from cyclic ketones

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5674-5676

  McAlpine, Indrawan J ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001200074     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960657w     Document Type: Article

References (11)

1. Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron Lett. 1963, 4, 2105, 2115.
2. Berlink, R. G. S.; Braekman, J. C.; Daloze, D.; Hallenga, K.; Ottinger, R.; Bruno, I.; Ricco, R. Tetrahedron Lett. 1990, 31, 6531.
3. Kato, T.; Shizuri, Y.; Izumida, H.; Yokoyama, A.; Endo, M. Tetrahedron Lett. 1995, 36, 2133.
4. Kinnel, R. B.; Gehrken, H.-P.; Scheuer, P. J. J. Am. Chem. Soc. 1993, 115, 3376.
5. Interestingly, Ugi points out that 2-thiohydantoin 4-imines are formed in high yield only from ketones and not from aldehydes, whereas, hydantoin 4-imines are formed from aldehydes but not very well from ketones (see ref 6).
6. Ugi, I. Isonitrile Chemistry; Academic Press: New York, 1971; Vol. 20, pp 145-155.
7. Ugi, I.; Rosendahl, F. R.; Bodesheim, F. Justus Liebigs Ann. Chem. 1963, 666, 54.
8. Meyers, A. I.; Shimano, M. Tetrahedron Lett. 1993, 34, 4893.
9. Robichaud, A. J.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607.
10. McKennon, M. J.; Meyers, A. I. J. Org. Chem. 1993, 58, 3568.
11. The hydroxythiourea 5 is somewhat unstable and rearranges upon standing, presumably to the 4-hydroxy-2-imino-3,1-thiazaspiro-[4]nonane.