Studies on lactams. Part XIII. A position isomer of a penam (4-thia-1-aza-bicyclo[3,2,0]heptane)
作者:Ajay K. Bose、G. Spiegelman、M. S. Manhas
DOI:10.1039/j39710000188
日期:——
Cycloaddition of azidoacetyl chloride and a 3-thiazoline has been used to synthesize the 6-azido-, 6-amino-, and 6-phthalimido- derivatives of a penam in which the position of the sulphur atom in the thiazolidine ring has been altered.
Dialkylphosphonates add in a 1,2 fashion to the C = N bond in 5,5-dimethyl-3-thiozolines 2 to form dialkyl rac-(4-thiazolidinyl)phosphonates 3a – e. Upon hydrolysis of 3arac-(1-amino-2-mercapto-2-methylpropyl)phosphonic acid (4a), the phosphonic acid analog of penicillamine (1), is formed.