Journal ArticleDOI
Polyfuryl(aryl)alkanes and their derivatives. 7. New recyclization and cyclization reactions in the 2-hydroxyaryldifurylmethane series
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In this paper, the reaction does not stop at the step involving formation of 2-hydroxyarylfuryl-methanes but proceeds further with opening of one of furan rings and recycling to 3-furylbenzo-furan derivatives.Abstract:
Reaction of 2-hydroxybenzaldehydes with α-methylfuran (sylvan) under acid-catalysis conditions was investigated. It is shown that the reaction does not stop at the step involving formation of 2-hydroxyarylfuryl-methanes but proceeds further with opening of one of furan rings and recyclization to 3-furylbenzo-furan derivatives. The latter in turn undergo transformations that lead to new heterocyclic systems — 5,6-dihydro-2,4-dimethyl-4-(5-methyl-2-furyl)-4H-benzo[b]furo[2,3-h]cyclopenta[b]furans. Data from the IR, PMR, and mass spectra, alternative synthesis, and x-ray diffraction analysis were used to confirm structures of the synthesized compounds.read more
Citations
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Journal ArticleDOI
Bis(5-alkyl-2-furyl)(2-carboxyphenyl)methanes for the synthesis of tetracyclic isochromone derivatives.
Journal ArticleDOI
The effect of an N-substituent on the recyclization of (2-aminoaryl)bis(5-tert-butyl-2-furyl)methanes: synthesis of 3-furylindoles and triketoindoles
TL;DR: In this paper, it was shown that the acid-catalyzed recycling of N -tosylamides leads to the formation of 2-(3-oxoalkyl)-3-(2-furyl)indoles.
Journal ArticleDOI
The Butin reaction
TL;DR: In this paper, a review summarizes the reported data on the Butin reaction, i.e., acid-catalyzed transformations of furans to a range of other heterocycles via intramolecular attack of nucleophile, connected to the α-carbon atom of furan ring by three- to six-membered linker.
Journal ArticleDOI
Simple and Convenient Synthesis of 4-Unsubstituted-3- (3-Oxoalkyl)isocoumarins
TL;DR: In this article, a simple transformation of 2−alkylfurans and 2−formylbenzoic acids into 4−unsubstituted 3−(3−oxoalkyl)isocoumarins is described.
Journal ArticleDOI
CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step
Anton S. Makarov,Anna E. Kekhvaeva,Christopher J. J. Hall,Danny Price,Igor V. Trushkov,Maxim G. Uchuskin +5 more
TL;DR: In this paper, a CuBr2-catalyzed alkylation of furans with a broad scope of benzyl alcohols and benzaldehydes was reported, and the reaction proceeds efficiently under mild reaction conditions requiring no inert atmosphere or other precautions.
References
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Mechanism of reactions of furans I: A kinetic study of the acid‐catalyzed hydrolysis of furan and 2,5‐dimethylfuran
TL;DR: In this paper, the first step is a slow proton transfer to the α-carbon atom of the furan ring, followed by a deuterium isotope effect, kH/kD, of 2,5-dimethylfuran.