Reactions of 3-acetyltropolone with benzaldehydes in trimethyl orthoformate in the presence of perchloric acid: Synthesis of 2-aryl-4-methoxy-9-oxocyclohepta[b]pyrylium perchlorates
✍ Scribed by Dao-Lin Wang; Kimiaki Imafuku
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 192 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
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‐methoxycinnamoyl)tropolone (5) were also isolated.
📜 SIMILAR VOLUMES
## 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
Reactions of biacetyl (¼ butane-2,3-dione) with (N-isocyanimino)triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford 3-(5-aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2-one derivatives in high yields. Introduction