SummaryA synthesis of (±)-cherylline dimethyl ether is reported. The key steps involved are Michael-type addition, radical azidonation of an aldehyde, Curtius rearrangement, and reduction of an isocyanate intermediate followed by Pictet–Spengler cyclization.

ABSTRACT. The synthesis of benzofuran based 1,3,4-thiadiazoles, 1,3,4-triazoles and 1,3,4-oxadiazole via cyclocondensation of thiosemicarbazides have been carried out by conventional and non-conventional methods in excellent yields of product.