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Synthesis and Reactivity of Phenylthiourea Derivatives: An Efficient Synthesis of New Thiazole‐Based Heterocycles
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Reaction of 1‐(5‐acetyl‐4‐methylthiazol–2‐yl)–3‐phenylthiourea 2 with hydrazonoyl chlorides (3a, 3b, 3c, 3d, 3e, 3f) and 9 yielded the corresponding (thiazolyl)imino–1,3,4‐thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f) and 12, respectively. Reaction of 2 with ethyl chloroacetate 13 gave (thiazolyl)imino‐1,3‐thiazolidin‐4‐one derivative 15, which upon condensation with aromatic aldehyde derivatives yielded the 5‐benzylidene derivatives (16a, 16b). In addition, treatment of 2 with 3‐chloropenta‐2,4‐dione 17 afforded the corresponding (thiazolyl)imino‐1,3‐thiazole derivative 19. The newly synthesized compounds were confirmed from their elemental analyses and spectral data.
Title: Synthesis and Reactivity of Phenylthiourea Derivatives: An Efficient Synthesis of New Thiazole‐Based Heterocycles
Description:
Reaction of 1‐(5‐acetyl‐4‐methylthiazol–2‐yl)–3‐phenylthiourea 2 with hydrazonoyl chlorides (3a, 3b, 3c, 3d, 3e, 3f) and 9 yielded the corresponding (thiazolyl)imino–1,3,4‐thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f) and 12, respectively.
Reaction of 2 with ethyl chloroacetate 13 gave (thiazolyl)imino‐1,3‐thiazolidin‐4‐one derivative 15, which upon condensation with aromatic aldehyde derivatives yielded the 5‐benzylidene derivatives (16a, 16b).
In addition, treatment of 2 with 3‐chloropenta‐2,4‐dione 17 afforded the corresponding (thiazolyl)imino‐1,3‐thiazole derivative 19.
The newly synthesized compounds were confirmed from their elemental analyses and spectral data.
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