A facile method for the synthesis of 1,3-oxathiolan-2-ones by reaction of oxiranes, sulfur, and carbon monoxide

Nishiyama, Yutaka; Katahira, Chisato; Sonoda, Noboru

doi:10.1016/j.tet.2006.03.081

Cited by 17 publications

(4 citation statements)

References 24 publications

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“…In addition to oxygen-based nucleophiles, sulfur- and carbon-based nucleophiles have also been employed in epoxide ring opening MCRs. Epoxides ( 75 ) underwent ring expansion to 1,3-oxathiolan-2-ones ( 76 ) by reaction with sulfur and carbon monoxide (Scheme ) . Sodium hydride and high pressures of CO (9.7 atm) were required to induce the transformation.…”

Section: Multicomponent Reactions With Heterocyclic Substratesmentioning

confidence: 99%

Small Heterocycles in Multicomponent Reactions

et al. 2014

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Section: Multicomponent Reactions With Heterocyclic Substratesmentioning

confidence: 99%

Small Heterocycles in Multicomponent Reactions

et al. 2014

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“…The three‐component reaction of epoxides 417 with sulfur under pressurized carbon monoxide in the presence of catalytic amounts of sodium hydride proceeds smoothly and provides the expected 1,3‐oxathiolan‐2‐ones 418 (Scheme ). For 2‐alkyl‐ and 2,2‐dialkyl‐substituted epoxides, 5‐alkyl‐ and 5,5‐dialkyl‐substituted 1,3‐oxathiolane‐2‐ones 418a and b were obtained in excellent yields …”

Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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“…Enantiomerically pure 1,3-thiazolidin-2-imine (R)-80 was successfully synthesized from chloromethyloxirane and N,N′-diphenylthiourea in the presence of ytterbium(III) trifluoromethanesulfonate [118] (Scheme 47). 1,3-Oxathiolan-2-ones were obtained by reaction of epoxides with sulfur and carbon(II) oxide [119]. Trisubstituted iminothiazolidines were also formed in reactions of epoxides with thiosemicarbazides [120].…”

Section: Synthesis Of 13-oxazolidin-2-ones From Isocyanates and Othementioning

confidence: 99%