Recent advances in iron(III) chloride catalyzed synthesis of heterocycles

Mishra, Mitali; Mohapatra, Seetaram; Mishra, Nilima Priyadarsini; Jena, Bighnanshu K.; Panda, Pravati; Nayak, Smita

doi:10.1016/j.tetlet.2019.07.016

Cited by 17 publications

(14 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[77][78][79][80] Also, there have been reports on cyclization of unsaturated intermediates through concerted efforts of iron II salts and diorganyl dichalcogenides. [81] Taking a cue from such reports, Zeni et al, [82] synthesized selenophene-fused chromene derivatives 23a-g (Scheme 9) through a step-wise cyclization of 1,3diynyl propargyl aryl ethers 22. The report showed that both dilution and temperature of substrate addition had a fundamental influence on the reaction outcome.…”

Section: Selenocyclofunctionalization Of Unsaturated Synthetic Intermmentioning

confidence: 99%

“…Selenophene synthesis frequently involve approaches or methods wherein the alkynes are subjected to addition and cyclization type of reactions in the presence of selenium catalyst, either as an electrophilic or nucleophilic species [77–80] . Also, there have been reports on cyclization of unsaturated intermediates through concerted efforts of iron II salts and diorganyl dichalcogenides [81] . Taking a cue from such reports, Zeni et al ., [82] synthesized selenophene‐fused chromene derivatives 23a – g (Scheme 9) through a step‐wise cyclization of 1,3‐diynyl propargyl aryl ethers 22 .…”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

See 1 more Smart Citation

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

View full text Add to dashboard Cite

The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

show abstract

Section: Selenocyclofunctionalization Of Unsaturated Synthetic Intermmentioning

confidence: 99%

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

View full text Add to dashboard Cite

show abstract

“…The syntheses of various biologically important Seheterocycles were successfully achieved by the electrophilic cyclization of alkynes using diorganyl diselenides and Fe(III) catalyst. [133][134][135][136] Scheme 78 shows the outline for the library of Se-heterocycles 235-240 via The iron(III) chloride and dibutyl diselenide 4 mediated cyclization of 1,3-diyne 241 leads to 3,4-bis (butylselanyl)selenophene 243 (Scheme 79). [137][138] The FeCl 3 (1.0 equiv.)…”

Section: Electrophilic Cyclization Of 13-diyne and 135-triynementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

show abstract

“…In synthetic organic transformation, metal-catalyzed reaction plays an important role in the synthesis of various functionalized cyclopropanes in the last few years. [11] These reactions include Zn, Mg, Cu, Pd, Rh catalyzed carbometalation, hydroboration, desymmetrization, hydroacylation, Overman rearrangement, allylmetalation, hydrostannation, hydrophosphorylation, and hydroformylation. But very recently (2016-20) we observed that similar types of reactions were reported just by changing the transition metal catalyst, varying ligand, and conditions of reactions with improved yield and stereoselectivity.…”

Section: Metal Catalyzed Functionalized Cyclopropane Synthesismentioning

confidence: 99%