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Hydrazidoyl halides in synthesis of Δ 2 ‐1,3,4‐selenadiazolin‐5‐ones
Author(s) -
Hassaneen Hamdi M.,
Shetta Abdelfattah,
Shawali Ahmad S.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170606
Subject(s) - chemistry , acetic anhydride , halide , yield (engineering) , benzoyl chloride , nitrosation , pyridine , medicinal chemistry , ethanol , potassium , chloride , organic chemistry , catalysis , materials science , metallurgy
Reaction of hydrazidoyl halides 1‐5 with potassium selenocyanate in ethanol produces the corresponding 2,4‐disubstituted‐5‐iminoδ 2 ‐1,3,4‐selenadiazolines, 9‐13 respectively. Nitrosation of the latter yields the N ‐nitroso derivatives 14‐17 , which decompose upon refluxing in xylene to give 2,4‐disubstituted Δ 2 ‐1,3,4‐selenadiazolin‐5‐ones in good yield. Compounds 9‐13 give the respective N ‐acetyl derivatives 22‐26 and N ‐benzoyl derivatives 27‐31 with acetic anhydride and benzoyl chloride in pyridine.