A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations.

doi:10.1039/c4ob01300j

Paper

A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations.

Published Oct 21, 2014 · Xiaobing Yang, Fangzhong Hu, Hongjing Di

Organic & biomolecular chemistry

Q2 SJR score

12

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols. In this strategy, these types of bases play an important role in driving the domino coupling reaction of propargyl alcohols and further intramolecular annulations to realize the target compounds. The possible mechanism for the formation of the various products is believed to involve the generation of allenes 7, followed by intramolecular annulations.

Study Snapshot

This study developed a convenient base-mediated strategy for synthesizing 3-aryol-4-methyl (or benzyl)-2-methylthio furans from -oxo ketene dithioacetals and propargyl alcohols, enabling the generation of allenes and

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations.

Sign up to use Study Snapshot

References

Highly efficient synthesis of 2,3,4-trisubstituted furans via silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes

Silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes efficiently synthesize 2,3,4-trisubstituted furans in a one-pot procedure.

One-pot straightforward approach to 2,3-disubstituted benzo/naphtho[b]furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone mediated by AlCl3 at room temperature

This one-pot method allows for the quick and easy production of 2,3-disubstituted benzo/naphtho[b]furans from readily available starting materials under mild reaction conditions.

Copper-catalyzed C-O bond formation: an efficient one-pot highly regioselective synthesis of furans from (2-furyl)carbene complexes.

Copper-catalyzed C-O bond formation offers a convenient one-pot strategy for regioselective synthesis of trisubstituted furan derivatives using air as an oxidant.

Recent developments of ketene dithioacetal chemistry.

Recent research on ketene dithioacetals has revealed new prospects and connections with various functional groups, aiding future organic synthesis designs.

Gold catalysis: catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers.

Gold catalysis can produce fluorene derivatives and indene derivatives, with the latter pathway relying on the aromatic moiety in the tether.

Regioselective synthesis of multisubstituted furans via metalloradical cyclization of alkynes with α-diazocarbonyls: construction of functionalized α-oligofurans.

The Co(P1)-catalyzed metalloradical cyclization reaction allows for the regioselective synthesis of polyfunctionalized furans with high functional group tolerance, making it a versatile tool for functionalizing -oligofurans.

Heterobimetallic Pd-Sn catalysis: a Suzuki, tandem ring-closing sequence toward indeno[2,1-b]thiophenes and indeno[2,1-b]indoles.

Heterobimetallic Pd-Sn catalysis enables the synthesis of indeno[2,1-b]thiophene and indeno[1,2-b]indole motifs from readily available nucleophiles, with potential applications in organic synthesis.

Gold-catalyzed synthesis of furans and furanones from sulfur ylides.

Gold-catalyzed synthesis of 3-carboxyfuran derivatives allows for the synthesis of bicyclic furans and quaternary center-containing furanones, with potential applications in organic synthesis.

Palladium-catalyzed synthesis of 2,3,4-trisubstituted furans via cascade reactions of aryloxy-enynes with aryl halides.

This method offers rapid access to 2,3,4-trisubstituted furans in good to excellent yields under mild reaction conditions, offering regioselective synthesis in a mild environment.

Citations