N-substituted derivatives of 3-carboxamide and 3-thiocarboxamide

Abstract

Compounds of the formula ##STR1## WHERE X represents O or S and R represents lower alkyl, cycloalkyl, phenyl or substituted phenyl wherein the substituents are selected from lower alkyl, lower alkoxy, halo and sulfonyl. The compounds are prepared by reacting the .[.carbinolamine.]. .Iadd.ring-opened intermediate,.Iaddend.obtained by reacting cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo (3,3,1,1 3 ,7) decane chloride with excess aqueous sodium hydroxide, with an equivalent amount of a corresponding R isocyanate or R isothiocyanate at a low temperature to give the substituted urea or thiourea product. The compounds have antimicrobial activity.

What is claimed is: 
     
       1. A compound corresponding to the formula ##STR6## wherein X represents O or S and R represents lower alkyl, 5 to 8 carbon atom cycloalkyl, phenyl or substituted-phenyl having lower alkyl, lower alkoxy, halo or sulfonyl substitution. 
     
     
       2. The compound of claim 1 wherein X represents O and R represents phenyl. 
     
     
       3. The compound of claim 1 wherein X represents S and R represents phenyl. 
     
     
       4. The compound of claim 1 wherein X represents O and R represents 4-methoxyphenyl. 
     
     
       5. The compound of claim 1 wherein X represents O and R represents 4-methylphenyl. 
     
     
       6. The compound of claim 1 wherein X represents O and R represents 2,5-dimethylphenyl. 
     
     
       7. The compound of claim 1 wherein X represents O and R represents 4-chlorophenyl. 
     
     
       8. The compound of claim 1 wherein X represents O and R represents 4-bromophenyl. 
     
     
       9. The compound of claim 1 wherein X represents O and R represents 2,5-dichlorophenyl. 
     
     
       10. The compound of claim 1 wherein X represents O and R represents 3,4-dichlorophenyl. 
     
     
       11. The compound of claim 1 wherein X represents O and R represents cyclohexyl. 
     
     
       12. The compound of claim 1 wherein X represents O and R represents 4-tolylsulfonyl. 
     
     
       13. The compound of claim 1 wherein X represents S and R represents 4-chlorophenyl. 
     
     
       14. The compound of claim 1 wherein X represents S and R represents 4-bromophenyl. 
     
     
       15. The compound of claim 1 wherein X represents S and R represents 3,4-dichlorophenyl. 
     
     
       16. The compound of claim 1 wherein X represents S and R represents 3,4-dimethylphenyl. 
     
     
       17. The compound of claim 1 wherein X represents O and R represents n-butyl. 
     
     
       18. The compound of claim 1 wherein X represents S and R represents n-butyl. 
     
     
       19. Method for making (a) a 7-cis(3-chloro-2-propenyl)-N-substituted-1,3,5,7-tetraazabicyclo(3.3.1)-nonane-3-carboxamide or (b) a 7-(3-chloro-2-propenyl)-N-substituted-1,3,5,7-tetraazabicyclo(3.3.1)nonane-3-thiocarboxamide which comprises adding (a) a substantially equimolar proportion of an R isocyanate in an organic solvent or (b) a substantially equimolar proportion of an R isothiocyanate in an organic solvent to an organic solvent solution of .[.3-hydroxymethyl-7-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo(3,3,1)nonane.]. .Iadd.the reaction product of Dowicil 200 with excess aqueous sodium hydroxide .Iaddend.at a reaction temperature between about minus 15 and about 5° C., wherein R represents lower alkyl, 5 to 8 carbon atom cycloalkyl, phenyl or substituted-phenyl wherein the substituents are selected from lower alkyl, lower alkoxy, halo and sulfonyl, and recovering the said product.