Solid Phase Synthesis and Application of Trisubstituted Thioureas

摘要

Resin-bound amines 1a-e condense with isothiocyanates to give thiourea resins 2a-i. Resins 2a-g subsequently react with iodomethane followed by cleavage affording S-methyl isothioureas 4a-g, and resins 2a-b, h-i react with acyl chlorides to afford N-acylated thioureas 6a-d, N-Acylthioureas 8a-f (R~2 = H) were prepared directly from resin-bound amines 1a-d with acyl isothiocyanates. N-Acylthioureas 8a-d, f (R~2 = H) were used for the preparation of S-methyl-N-acylisothioureas 10a-e. Alkylation was performed suing methyl iodide. Resin-bound S-methyl-N-acylisothioureas 10a, b, d are converted by an action of hydrazines into 3-amino-1,2,4-triazoles 13a-d. Condensation of resins 8a-e (R~2 = H) with 2-bromoacetophenones in the presence of TEA affords thiazoles 15a-e. All transformations proceeded in high yields and gave products of good purities.