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Preparation of 1,2,5‐thiadiazole‐3‐carboxaldehydes
Author(s) -
Matakas Shuntaro,
Kurisu Masayoshi,
Takahashi Kazufumi,
Tashiro Masashi
Publication year - 1985
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.5570220219
Subject(s) - chemistry , halogenation , thiadiazoles , organic chemistry , thermal decomposition , decomposition , pyrolysis , medicinal chemistry
1,2,5‐Thiadiazole‐3‐carboxaldehydes 1a‐c were prepared by the acid‐catalyzed decomposition of 3‐azido‐methyl‐1,2,5‐thiadiazoles 2a‐c in 68‐83% yields, respectively. Pyrolysis of 2a and 2b afforded the imidazoles 4a and 4b in low yields. NBS ‐bromination of 1a and 1b gave the corresponding carboxylic acids 10a and 10b via acid bromides 9. Azides 2a and 2b gave the s ‐triazines 8a and 8b on treatment with NBS.