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Synthesis and reactivity of 6-methyl-4H-furo[3,2c]pyran-3,4-dione

✍ Scribed by Djamila Hikem-Oukacha; Yahïa Rachedi; Maamar Hamdi; Artur M.S. Silva

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
141 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

An efficient synthesis of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one by bromination of dehydroacetic acid in glacial acetic acid is described. Novel 4‐hydroxy‐6‐methyl‐3‐(2‐substituted‐thiazol‐4‐yl)‐2__H__‐pyran‐2‐ones have been prepared from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one with thioamides, thiourea, and diphenylthiocarbazone. The condensation reaction of 6‐methyl‐4__H__‐furo[3,2__c__]pyran‐3,4‐dione, obtained from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one with aliphatic amines, with benzaldehydes and acetophenones led to novel 2‐arylidene‐6‐methyl‐2__H__‐furo[3,2‐c]pyran‐3,4‐diones and 6‐(2‐arylprop‐1‐enyl)‐2__H__‐furo[3,2‐c]pyran‐3,4‐diones. The structure of all compounds was established by elemental analysis, IR, NMR, and mass spectra. J. Heterocyclic Chem., 2011.

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Multicomponent Reactions of Furan-2,3-di
Multicomponent Reactions of Furan-2,3-diones: Synthesis and Characterizations of Furo[3,2-c]pyran-4-ones
✍ İrfan Koca; İsmail Yıldırım; Ertan Şahin 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 German ⚖ 236 KB 👁 1 views

## Abstract Furo[3,2‐__c__]pyran‐4‐ones, which possess a natural‐product skeleton, are synthesized __via__ a simple, one‐pot, three‐component reaction of furan‐2,3‐diones with dialkyl acetylenedicarboxylates and Ph~3~P.