A synthesis of novel three‐, four‐, and sixfold branched 4‐phenylthiazolylhydrazones, 4‐pyrazolylthiazolyl hydrazones, and thiadiazoles which are linked to a benzene core via phenoxymethyl spacers was reported. The synthetic methodology includes initially formation of poly(aldehyde thiosemicarbazones) 9, 14, and 15 by acid catalyzed condensation of thiosemicarbazide (8) with the appropriate poly(aldehydes) 3, 5, and 7, respectively. Subsequent reaction of 9, 14, and 15 with each of 2‐bromo‐1‐phenylethanone (10a) and 2‐bromo‐1‐(4‐chlorophenyl)ethanone (10b) in refluxing ethanol in the presence of few drops of TEA afforded 11, 16, and 18, respectively, in good yields. On the other hand, the synthesis of the novel poly(4,5‐dihydro‐1,3,4‐thiadiazolyl) derivatives 20, 21a,21b, and 22 was performed by cyclization of 9b, 14a,14b, and 15a, respectively, in refluxing acetic anhydride.