Reactions of 2-aryl-4-methoxy-9-oxocyclohepta[b]pyrylium perchlorates with hydroxylamine and hydrazines
✍ Scribed by Dao-Lin Wang; Kimiaki Imafuku
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 360 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
2‐Aryl‐4‐methoxy‐9‐oxocyclohepta[b]pyrylium perchlorates 1a‐c reacted with hydroxylamine hydrochloride and hydrazine sulfate in the presence of triethylamine to afford 2‐aryl‐4,9‐dihydrocyclohepta[b]pyran‐4,9‐dione 4‐oximes 3a‐c and 4‐hydrazones 4a‐c in good yields, respectively. On the other hand, the reactions with methylhydrazine and phenylhydrazine gave respectively 1‐methyl‐ and 1‐phenyl‐substituted 5‐aryl‐3‐(3‐tropolonyl)pyrazoles 5a‐c and 6a‐c in excellent yields. Treatment with 4‐nitrophenylhydrazine gave 2‐aryl‐4,9‐dihydrocyclohepta[b]pyran‐4,9‐dione 4‐(4‐nitrophenyl)hydrazones 7a‐c in good yields.
📜 SIMILAR VOLUMES
## Abstract 3‐Acetyltropolone (1) reacted with benzaldehydes in trimethyl orthoformate in the presence of perchloric acid to afford 2‐aryl‐4‐methoxy‐9‐oxocyclohepta[__b__]pyrylium perchlorates 3a‐c in 25–37% yields. From the filtrates, 3‐(3,4‐diaryl‐3‐butenoyl)tropolones 4a,b and 3‐(2‐methoxycinnam