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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.


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Reactions of 2-aryl-4-methoxy-9-oxocyclo
✍ Dao-Lin Wang; Kimiaki Imafuku 📂 Article 📅 1998 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 360 KB

## 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

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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