A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides

Kobeissi, Marwan; Yazbeck, Ogaritte; Chreim, Yamama

doi:10.1016/j.tetlet.2014.03.021

Cited by 13 publications

(11 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Overall, the more nucleophilic aliphatic amines 2b – d afford the amidation products in higher yields; in contrast, the less nucleophilic aromatic amine 2a provide a slightly lower yield. The results obtained with p -toluidine were in good agreement with the yields of the amidation products by using succinic acid and also previously reported literature data …”

Section: Results and Discussionsupporting

confidence: 90%

“…The results obtained with p-toluidine were in good agreement with the yields of the amidation products by using succinic acid and also previously reported literature data. 38 On the basis of the results in Figure 7, different nonactivated carboxylic acids were subsequently explored as more challenging amidation reactions. Albeit benzylamine 2e is slightly less nucleophilic than 2-ethyl-1-hexylamine 2b, 39 benzylamine was employed due to its accessibility, higher boiling point, and possibility to detect under UV irradiation, thereby facilitating reaction monitoring and purification by flash column chromatography.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Chaparro

Rojas

Castillo

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Biogenic carbonates were studied as catalysts in this work for the direct synthesis of amides under solvent-free conditions. Solids were synthesized by microbial coprecipitation of CaCl 2 and Ni salts and Cu and Fe salts. The catalysts were characterized by thermogravimetric analysis, nitrogen physisorption measurements, X-ray diffraction, and X-ray photoelectron spectroscopy. The polymorphism, hydrophilicity, and textural properties depended on the metal oxides type incorporated on CaCO 3 . N-Arylsuccinimides synthesis was employed as test reaction, obtaining remarkable selectivity and conversion in the reaction of succinic acid with p-toluidine and aniline, respectively. Optimized conditions were subsequently extended to the solvent-free synthesis of diverse amides in good yields using CuO−CaCO 3 as the catalyst in air. The direct amidation protocol was amenable to the use of different primary amines and nonactivated carboxylic acids.

show abstract

Section: Results and Discussionsupporting

confidence: 90%

Section: ■ Introductionmentioning

confidence: 99%

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Chaparro

Rojas

Castillo

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…1 H NMR (400 MHz, CDCl 3 ): δ 7.50–7.45 (m, 2H), 7.41–7.37 (m, 1H), 7.29–7.26 (m, 2H), 2.87 (s, 4H) ppm. The spectral data match those previously reported …”

Section: Methodssupporting

confidence: 89%

“…13 C{ 1 H} NMR (100 MHz, acetone-d6):  = 167.6, 154.5, 135.3, 134.0, 133.8, 133.3, 124.1, 121.9, 119.4, 111.0 ppm. MS (EI): m/z = 317 (M + , 34), 273 (82), 104 (60), 76 (100), 50(34). The spectral data match those previously reported 42.…”

supporting

confidence: 83%

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

et al. 2019

View full text Add to dashboard Cite

We report on cyclic imides as weak directing groups for selective mono-hydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp 2)-H bond enabling 5-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp 2)-H bond via a larger 6-membered ruthenacycle intermediates. Furthermore, mono-hydroxylated products were exclusively obtained (even in the presence of over-stoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate co-planar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.  ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publications website at DOI: XXX. Screening of reaction conditions, computational details and NMR spectra (PDF) Crystallographic data for 2b (CCDC-187307, CIF) Crystallographic data for 2d (CCDC-1873708, CIF)  AUTHOR INFORMATION

show abstract

“…followed by acid-catalyzed rearrangement [900]. The first successful X-ray crystal structure of the Tebbe reagent (cocrystallized with Cp 2 Ti(µ-Cl) 2 AlMe 2 ) was reported [901].…”

Section: )mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

View full text Add to dashboard Cite

A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides

Cited by 13 publications

References 28 publications

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Contact Info

Product

Resources

About

A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides

Cited by 13 publications

References 28 publications

Solventless Amide Synthesis Catalyzed by Biogenic CaCO3 Materials

Solventless Amide Synthesis Catalyzed by Biogenic CaCO3 Materials

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Contact Info

Product

Resources

About

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials