Modified One-Pot Multicomponent Diastereoselective Synthesis of <i>Trans</i>-2,3-Dihydrofuro[3,2-c]coumarins via In Situ–Generated <font>α</font>-Tosyloxyketones

Kumar, Ravi; Wadhwa, Deepak; Hussain, Khalid; Prakash, Om

doi:10.1080/00397911.2012.671435

Cited by 14 publications

(6 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…34 A modified protocol for diastereoselective synthesis of differently substituted trans-2,3-dihydrofuro[3,2-c]coumarins was developed by a one-pot MCR via in situ-generated αtosyloxyketones in the presence of pyridine and trimethylamine catalyzers. 35 Samant et al reported the results of the MCR reaction of 4-hydroxycoumarin, aldehydes, and 2-bromo-1-phenylethanone to prepare trans-2,3-dihydrofuro[3,2-c]coumarins using 4-dimethylaminopyridine (DMAP) as an efficient and environmentally benign catalyst. The reaction was further accelerated by microwaves.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and application of monodisperse poly L-Dopa microspheres

Havasian¹,

Heydaripour²,

Nateghi³

et al. 2018

Turk J Chem

View full text Add to dashboard Cite

In this study, 3,4-dihydroxy-L-phenylalanine (L-Dopa) was solvothermally polymerized to monodisperse microspheres 1 µ m in diameter. Polymerization was carried out in dimethylformamide containing appropriate amounts of urea and L-Dopa at 120 • C for 24 h. Synthesis of the polymer in basic aqueous solution under hydrothermal conditions or via conventional heating resulted in the formation of bulky powders including irregularly shaped particles of the polymer. The morphologies of the synthesized polymers were characterized by scanning electron microscopy (SEM). The microspheres synthesized by solvothermal method (with ∼ 1 µ m average diameter) were clearly observable in SEM micrographs. The thermal stability of the synthesized polymer was studied by thermogravimetry and differential scanning calorimetry techniques. It was recognized that the polymer is thermally stable at more than 200 • C. Applicability of the polymer microspheres was investigated for catalyzing the reaction of one-pot multicomponent synthesis of dihydrofurans. Several dihydrofuran derivatives were successfully synthesized using poly L-Dopa as a novel, environmentally friendly, and efficient catalyst with efficiency of more than 90%. Poly L-Dopa is easily separated by filtration from the reaction mixture. It can be used several times without decreasing the catalyzing activity after washing by suitable solvents.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and application of monodisperse poly L-Dopa microspheres

Havasian¹,

Heydaripour²,

Nateghi³

et al. 2018

Turk J Chem

View full text Add to dashboard Cite

show abstract

“…Prakash and Aneja [17] demonstrated the synthetic equivalency of these compounds by achieving successful synthesis of useful thiazole derivatives. Other significant reports highlighting the synthetic equivalency of α-tosyloxyketones and α-haloketones are, (i) isolation of synthetically useful furocoumarins by the reaction of α-tosyloxyketones with 4-hydroxycoumarin [18], (ii) diastereoselective synthesis of differently substituted trans -2,3-dihydrofuro[3,2-c]coumarins [19] and (iii) synthesis of polysubstituted oxazoles via decarboxylative oxidative cyclization of primary amino acids and α-tosyloxyketones [20].…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Polysubstituted Cyclopropanes Using a-Tosyloxyketones

Rana¹,

Nain²,

Kumar³

et al. 2018

Asian J. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The reaction comprises the treatment α‐tosyloxyketones 4 with 4‐hydroxycoumarin and different substituted aromatic aldehydes 65 (Scheme 22). [62] …”

Section: Synthesis Of Heterocyclic Compounds Via Tosyloxylation Of Ketonesmentioning

confidence: 99%

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

et al. 2022

View full text Add to dashboard Cite

Organo hypervalent iodine reagents are nowadays more attractive and versatile reagents for various chemical transformations in synthetic organic chemistry. These reagents are milder and having similar reactivity compared with toxic heavy metal reagents. Organo hypervalent iodine (λ3) reagents are successfully utilized to prepare synthetically and biologically important heterocycles. Hydroxy(tosyloxy)iodobenzene (HTIB) also acknowledged as Koser's reagent uses as an environmentally sustainable alternative to toxic heavy metals for the numerous and valuable organic transformations. The goal of this review is to highlight the recent advancements of the HTIB especially in the construction of heterocycles with various substitution patterns in a well‐organized form via tosyloxylation of ketones and oxidative cyclization methodology. This review compiles the up‐to‐date synthetic advancements of HTIB in the field of heterocycles.

show abstract

Modified One-Pot Multicomponent Diastereoselective Synthesis of Trans-2,3-Dihydrofuro[3,2-c]coumarins via In Situ–Generated α-Tosyloxyketones

Cited by 14 publications

References 9 publications

Synthesis, characterization, and application of monodisperse poly L-Dopa microspheres

Synthesis, characterization, and application of monodisperse poly L-Dopa microspheres

Facile Synthesis of Polysubstituted Cyclopropanes Using a-Tosyloxyketones

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

Contact Info

Product

Resources

About