N- And S-Alkylation of 3-(1-Aadamantyl)-4-methyl-1,2,4-triazole-5-thiol and 2-(1-Adamantyl)-1,3,4-oxadiazole-5-thiol

ABSTRACT

-The reaction of 3-(1-adamantyl)-4-methyl-1,2,4-triazole-5-thiol 1 with certain 2-aminoethyl chlorides in alkaline medium yielded a separable mixture of the S-(2-aminoethyl) derivatives 2 and the N-(2-aminoethyl) derivatives 3. Meanwhile, alkylation of 2-(1-adamantyl)-1,3,4-oxadiazole-5-thiol 4 with 2-aminoethyl chlorides under the same conditions yielded only the S-alkyl derivatives 5. Interaction of 4 with primary or secondary amines and formaldehyde solution yielded the corresponding N-aminomethyl derivatives in high yields.

KEY WORDS:

• Adamantane Derivatives
• 1,2,4-Triazoles-5-thiol
• 1,3,4-Oxadiazole-5-thiol