N-ALKYLATION AND S-ALKYLATION OF 3-(1-ADAMANTYL)-4-METHYL-1,2,4-TRIAZOLE-5-THIOL AND 2-(1-ADAMANTYL)-1,3,4-OXADIAZOLE-5-THIOL

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-oxadia zole-5-thiol 4 with 2-aminoethyl chlorides under the same conditions y ielded only the S-alkyl derivatives 5. Interaction of 4 with primary o r secondary amines and formaldehyde solution yielded the corresponding N-aminomethyl derivatives in high yields.