Novel epoxide formation in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol

Lam, Tom M.; Lee, Chain; Katardjieff, Katherine; Otsuki, Tetsuo

doi:10.1016/j.bmcl.2010.10.098

Cited by 4 publications

(2 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,4‐Dihydro‐1,4‐dioxonaphtho[ b ‐2,3]‐1,4‐dithiacycloheptene (7) and S ‐{3‐[(1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)thio]propyl} ethanethioate (8) : To a solution of the 1,3‐dibromopropane (100 mg, 0.50 mmol) in MeOH (0.1 m ) were added potassium thioacetate (120 mg, 1.05 mmol) and Yb(OTf) 3 (6 mg, 2 mol %), and the resulting mixture was stirred at 70 °C under nitrogen. After 12 h, the mixture was cooled to room temperature, and naphthalene‐1,4‐dione (158 mg, 1.0 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Huang

Liang

2018

Asian J Org Chem

View full text Add to dashboard Cite

Ay tterbium(III) trifluoromethanesulfonate catalyzed one-pot three-component thia-Michael addition reaction of thiolate salts, organic halides, and a,b-unsaturated compoundsh as been developed for the formationo f carbon-sulfur bonds. In this study,p otassium thioacetate serves as the sulfur source in an ucleophilic substitution reaction, which is followed by aY b(OTf) 3 -catalyzed (OTf = trifluoromethanesulfonate) S-deacetylation and subsequent thia-Michael addition reaction. Three important pharmaceutical derivatives were successfully prepared by using the intramolecular version of this one-pot thia-Michael addition reaction. The advantages of this Yb III -catalyzed process include its operational simplicity,i ts capacity towards the preparation of structurally diverse products in 40-93 %y ield, itsu se of relativelyl ow toxic or nontoxic reagents, and its catalyst loading of only 1-2 mol %.Scheme1.Synthetic methods for thia-Michael addition (EWG = electronwithdrawing group, SDS = sodium dodecyls ulfate, Ts = para-toluenesulfonyl, and PEG = polyethylene glycol).

show abstract

Section: Methodsmentioning

confidence: 99%

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Huang

Liang

2018

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…[1][2][3] The preparation of thiol-protected molecules andt he removal of thiol protecting groups have become increasingly important in the development of new syntheticm ethods. For example, thiol functional groups have been applied to intramolecular cyclization, [4] intermolecular polymerization, [5] thiol-ene click chemistry, [3] and metal-catalyzed couplingr eactions. [6] Moreover,s pontaneous assemblies of organic thiols on nanoparticulate composites are an important tool for chemists and surface scientists with applications in various fields, including self-assembled monolayer (SAM) films, [7] sensors, [8] electronics, [9] and biomedicine.…”

Section: Introductionmentioning

confidence: 99%

Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)₃

et al. 2017

View full text Add to dashboard Cite

The dysprosium(III)-trifluoromethanesulfonate-catalyzed S-deacetylation and selective S-deacetylation reactions of functionalized thioesters could be tuned by changing the reactionm edium or through the inclusiono fa dditives. In this study,t he deprotection of thioacetates by using catalytic amounts of Dy(OTf) 3 under mild heating resultedi n high yields of the free thiols without the formation of disulfide byproducts, whilst the selective S-deacetylation reaction by using ac ombination of catalytic amounts of Dy(OTf) 3 and NaHCO 3 afforded the products in moderate-to-excellent yields. Moreover,g lycosyl 1-thioacetate was selectively S-deacetylated at the anomeric position in ac o-solvent system. Notably,D y(OTf) 3 is an environmentally friendly catalyst, and ar ecycling strategy was successfully employed for the S-deacetylation reaction.

show abstract

ChemInform Abstract: Novel Epoxide Formation in the Reaction of 2‐Bromo‐3‐methyl‐1,4‐naphthoquinone with 1,3‐Propanedithiol.

et al. 2011

View full text Add to dashboard Cite

Novel Epoxide Formation in the Reaction of 2-Bromo-3-methyl-1,4-naphthoquinone with 1,3-Propanedithiol. -Epoxide (III) is formed as the major product in the microwave-assisted reaction of naphthoquinone (I) with propanedithiol (II) in the presence of triethylamine. Molecular oxygen might be the source of the added oxygen in (III), an oxidation product of its precursor (V). Only a strong base such as triethylamine is able to abstract the methyl hydrogen of naphthoquinones leading to the formation of (V) as well as (III). On the other hand, performing this reaction at different temperatures leads to a different distribution of the reaction products. Beside the main products, in one case, formation of a spiro compound (VI) is observed. -(LAM, T. M.; LEE, C.; KATARDJIEFF, K.; OTSUKI*, T.; Bioorg. Med. Chem. Lett. 20 (2010) 24, 7226-7229, http://dx.

show abstract

Novel epoxide formation in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol

Cited by 4 publications

References 6 publications

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)₃

ChemInform Abstract: Novel Epoxide Formation in the Reaction of 2‐Bromo‐3‐methyl‐1,4‐naphthoquinone with 1,3‐Propanedithiol.

Contact Info

Product

Resources

About

Novel epoxide formation in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol

Cited by 4 publications

References 6 publications

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)3

ChemInform Abstract: Novel Epoxide Formation in the Reaction of 2‐Bromo‐3‐methyl‐1,4‐naphthoquinone with 1,3‐Propanedithiol.

Contact Info

Product

Resources

About

Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)₃