Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

Shirini, Farhad; Mazloumi, Masoumeh; Seddighi, Mohadeseh

doi:10.1007/s11164-015-2116-0

Cited by 28 publications

(9 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fractions containing the product (TLC) were pooled and evaporated to afford an off-white solid 27a in 79% yield. mp 210.3–213.5 °C (lit 37 210–212 °C); TLC Rf 0.30 (CHCl 3 : MeOH, 20:1); 1 H NMR (DMSO-d 6 ) δ7.52 (s, 4H, ArH), 8.23 (d, J = 1.91 Hz, 2H, exch, CHO), 10.15 (s, 2H, exch, NH).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Structure based drug design and in vitro metabolism study: Discovery of N-(4-methylthiophenyl)-N,2-dimethyl-cyclopenta[d]pyrimidine as a potent microtubule targeting agent

Xiang

Choudhary

Hamel

et al. 2018

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

We report a series of tubulin targeting agents, some of which demonstrate potent antiproliferative activities. These analogs were designed to optimize the antiproliferative activity of 1 by varying the heteroatom substituent at the 4'-position, the basicity of the 4-position amino moiety, and conformational restriction. The potential metabolites of the active compounds were also synthesized. Some compounds demonstrated single digit nanomolar IC values for antiproliferative effects in MDA-MB-435 melanoma cells. Particularly, the S-methyl analog 3 was more potent than 1 in MDA-MB-435 cells (IC = 4.6 nM). Incubation of 3 with human liver microsomes showed that the primary metabolite of the S-methyl moiety of 3 was the methyl sulfinyl group, as in analog 5. This metabolite was equipotent with the lead compound 1 in MDA-MB-435 cells (IC = 7.9 nM). Molecular modeling and electrostatic surface area were determined to explain the activities of the analogs. Most of the potent compounds overcome multiple mechanisms of drug resistance and compound 3 emerged as the lead compound for further SAR and preclinical development.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Compound 27b was synthesized from 26b following the procedure of 27a , and it was obtained as an off-white solid in 78% yield. mp 136.7–138.2 °C (lit 37 mp 138–141 °C); TLC Rf 0.44 (CHCl 3 : MeOH, 20:1); 1 H NMR (CDCl 3 ) δ3.33 (s, 3H, NCH 3 ), 7.17–7.28 (m, 4H, ArH), 7.46 (br, 1H, exch, NH), 8.47 (s, 2H, exch, CHO).…”

Section: Methodsmentioning

confidence: 99%

Structure based drug design and in vitro metabolism study: Discovery of N-(4-methylthiophenyl)-N,2-dimethyl-cyclopenta[d]pyrimidine as a potent microtubule targeting agent

Xiang

Choudhary

Hamel

et al. 2018

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…Optimization of the reaction conditions for the synthesis of formamidine (entries [1][2][3][4][5][6][7][8] and N, N'-diaryl formamidine (entries [9][10][11][12][13][14] derivatives. 192-194 [48] 4,4'-sulfonyldianiline [d] 3 m 20 15 97 100-101…”

Section: Catalytic Activitymentioning

confidence: 99%

“…102 [48] C 102 [19] ( reaction was completed, water was added to the reaction mixture in order to dissolve the catalyst. Then the reaction mixture was filtered off and the filtrate was evaporated under vacuum up to 70°C to the white solid residue achieved.…”

Section: Entrymentioning

confidence: 99%

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

et al. 2020

Self Cite

View full text Add to dashboard Cite

In this study, two recently reported 1,4-diazabicyclo[2.2.2] octane (DABCO)-based ionic liquids were used for the acceleration of the N-formylation of primary and secondary amines with formic acid under solvent-free conditions. These reagents have also been used for the efficient synthesis of N, N'-diaryl formamidines through reaction of triethyl orthoformate with primary aryl amines. These methods offer several advantages such as excellent yields, short reaction times and simple workup with the environmentally friendly procedure.

show abstract

“…13 C CPMAS NMR spectra of silica xerogel are shown in Fig.2 Fig.3 (a-b). In functionalized silica xerogels spectra revealed characteristic silica and RTIL bands at around 3305 cm -1 (-OH group), 1635 cm-1 (Si-OH and H-O-H), 1050 cm −1 (Si-O-Si) and 790 cm −1 (Si-O) and 1634 (C═N imidazole) [49][50][51] . PU formation was observed by means of characteristic PU bands [52][53][54] at around 2936 -2840 cm −1 (C-H), 1532 cm −1 (HN), 1246 cm −1 (C-N and C-O of urethane), 1100 cm −1 (C-O-C), 3350 cm −1 (N-H of bonded hydrogen) and 1727 cm −1 (C=O).…”

Section: Co 2 Sorption Measurementsmentioning

confidence: 99%

Polyurethane /Ionic Silica Xerogel Composites for CO2 Capture

et al. 2019

View full text Add to dashboard Cite

Capturing carbon dioxide (CO 2) from exhaust gases is an important strategy to prevent climate change. There is a great interest in developing novel CO 2 sorbents. Thus, a series of polyurethane (PU) / silica xerogels functionalized with RTILs (bmim Cl and bmim TF 2 N) composites were prepared and characterized. PU matrix was reinforced with functionalized silica xerogels in the range of 0.5-20 wt%. PU / functionalized silica xerogels were characterized by NMR, FTIR, DSC, TGA, DMTA and FESEM. CO 2 sorption capacity and reusability were assessed by the pressure-decay technique at 298.15 K and 1 bar. Results showed that the filler aggregation in PU matrix promoted the reduction of mechanical properties. However, addition of silica xerogels functionalized with RTILs in PU matrix led to increased CO 2 uptake. CO 2 sorption capacity tends to increase with the incorporation of silica xerogels functionalized with RTILs in PU matrix. The best CO 2 sorption value was found for PU/SX-[Bmim]-[TF 2 N] 0.5 composite (48.5 mgCO 2 /g at 298.15 K and 1 bar). Moreover, the PU/SX-[Bmim]-[TF 2 N] 0.5 composite showed reuse capacity and higher CO 2 sorption value as compared to other reported composites.

show abstract

Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

Cited by 28 publications

References 41 publications

Structure based drug design and in vitro metabolism study: Discovery of N-(4-methylthiophenyl)-N,2-dimethyl-cyclopenta[d]pyrimidine as a potent microtubule targeting agent

Structure based drug design and in vitro metabolism study: Discovery of N-(4-methylthiophenyl)-N,2-dimethyl-cyclopenta[d]pyrimidine as a potent microtubule targeting agent

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

Polyurethane /Ionic Silica Xerogel Composites for CO2 Capture

Contact Info

Product

Resources

About