Diastereoselective and Reversed Regioselective Annulations of N-Alkyl Anilines to Julolidines and Lilolidines DOI
Sumana Mandal, Subhajit Saha, Chandan K. Jana

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4883 - 4887

Published: June 10, 2020

A three-component annulation reaction of N-alkyl anilines, cyclic 1,3-dicarbonyl compounds, and aryl aldehydes to julolidines lilolidines is reported. The 6π-electrocyclization enabled the proceed with reversed regioselectivity as compared that occurs in Povarov reaction. Both acyclic anilines participated provide a wide range single regio- diastereoisomers good excellent yields.

Language: Английский

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation DOI

P. J. Llabres-Campaner,

Rafael Ballesteros‐Garrido, Rafaél Ballesteros

et al.

The Journal of Organic Chemistry, Journal Year: 2017, Volume and Issue: 83(1), P. 521 - 526

Published: Dec. 12, 2017

The development of original strategies for the preparation indole derivatives is a major goal in drug design. Herein, we report first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order achieve high selectivity, combination Pt/Al2O3 ZnO have been found slowly dehydrogenate generating, after condensation with amine tautomeric equilibrium, corresponding pyrrole-ring unsubstituted indoles.

Language: Английский

Citations

32

Production of 1,3-Propanediol from Pure and Crude Glycerol Using Immobilized Clostridium butyricum DOI Open Access

Igor Dolejš,

Monika Líšková,

Vladimír Krasňan

et al.

Catalysts, Journal Year: 2019, Volume and Issue: 9(4), P. 317 - 317

Published: March 31, 2019

The present study describes the production of value-added chemical 1,3-propanediol (1,3-PD) from crude glycerol, a waste by-product formed during biodiesel production. efficiency, robustness, and stability process were improved by immobilization anaerobic bacterium Clostridium butyricum into polyvinyl alcohol (PVA) hydrogel. highest average productivity, 6.8 ± 0.2 g/(L·h), was achieved in 10 consecutive, repeated batch fermentations, with an initial concentration pure glycerol 45.5 0.7 g/L, after 2.5 h. final yield 1,3-PD, 28.3 0.6 0.42 0.01 g/g, respectively, eleven increasing to 70.4 1.9 g/L. Two different types produced used cooking oil (UCO) rapeseed (RO), tested productivity 2.3 0.1 3.5 0.3 respectively. 12.6 0.9 0.35 0.02 observed fifteen fermentations RO glycerol. An excellent immobilized bacteria increase fermentation demonstrated.

Language: Английский

Citations

27

Microwave-assisted multicomponent synthesis of julolidines using silica-supported calix[4]arene as heterogeneous catalyst DOI
Walysson Ferreira de Paiva, Ingredy Bastos Braga, João Vítor de Assis

et al.

Tetrahedron, Journal Year: 2019, Volume and Issue: 75(27), P. 3740 - 3750

Published: May 29, 2019

Language: Английский

Citations

25

Glycerol Upgrading via Hydrogen Borrowing: Direct Ruthenium-Catalyzed Amination of the Glycerol Derivative Solketal DOI Creative Commons
Anna Said Stålsmeden, José L. Belmonte‐Vázquez,

Kim van Weerdenburg

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2016, Volume and Issue: 4(10), P. 5730 - 5736

Published: Aug. 31, 2016

Hydrogen borrowing provides an efficient and atom economical method for carbon–nitrogen carbon–carbon bond formation from alcohol precursors. Glycerol is a renewable nontoxic polyol potential precursor to small functional organic molecules. We here report the direct amination of solketal, 1,2-hydroxy-protected derivative glycerol, via ruthenium-catalyzed hydrogen borrowing, affording up 99% conversion 92% isolated yield using [Ru(p-cymene)Cl2]2 as catalyst precursor. The synthesis antitussive agent in 86% overall solketal was also demonstrated this methodology.

Language: Английский

Citations

23

Combining bio- and chemo-catalysis for the conversion of bio-renewable alcohols: homogeneous iridium catalysed hydrogen transfer initiated dehydration of 1,3-propanediol to aldehydes DOI
Yueming Wang, Fabio Lorenzini, Martin Rebroš

et al.

Green Chemistry, Journal Year: 2015, Volume and Issue: 18(6), P. 1751 - 1761

Published: Nov. 9, 2015

The hydrogen transfer initiated dehydration of 1,3-propanadiol to propionaldehyde, catalysed by a highly recyclable, air and water stable, soluble Ir(iii) complex, in an ionic liquid, was demonstrated.

Language: Английский

Citations

24

Ruthenium(ii) and iridium(iii) complexes featuring NHC–sulfonate chelate DOI

A. Rajaraman,

Apurba Ranjan Sahoo,

Frédéric Hild

et al.

Dalton Transactions, Journal Year: 2015, Volume and Issue: 44(40), P. 17467 - 17472

Published: Jan. 1, 2015

Three new complexes bearing a chelating (κ2C,O) NHC-SO3 ligand have been prepared.

Language: Английский

Citations

18

Molecular and heterogenized dinuclear Ir-Cp* water oxidation catalysts bearing EDTA or EDTMP as bridging and anchoring ligands DOI
Chiara Domestici, Leonardo Tensi, Francesco Zaccaria

et al.

Science Bulletin, Journal Year: 2020, Volume and Issue: 65(19), P. 1614 - 1625

Published: June 12, 2020

Language: Английский

Citations

15

Co(dppbsa)-catalyzed reductive N,N-dimethylation of nitroaromatics with CO2 and hydrosilane DOI

Shuangshuang Ma,

Rui Sun, Ziheng Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8625 - 8632

Published: Jan. 1, 2023

A novel half-sandwich Co(dppbsa) ([Co]) was synthesized and employed for the catalytic N , -dimethylation of nitroaromatics with CO 2 hydrosilane. The same catalyst also enabled highly efficient reduction to aromatic amines.

Language: Английский

Citations

5

Synthesis and structural characterisation of 1’-(diphenylphosphino)ferrocene-1-phosphonic acid, its ammonium salts and Pd(II) complexes DOI
Filip Horký, Ivana Cı́sařová, Jiří Schulz

et al.

Journal of Organometallic Chemistry, Journal Year: 2019, Volume and Issue: 891, P. 44 - 53

Published: April 17, 2019

Language: Английский

Citations

14

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines DOI
Delia Bellezza, Ramón J. Zaragozá, M. José Aurell

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 19(3), P. 677 - 683

Published: Dec. 17, 2020

The use of diols and anilines as reagents for the preparation indoles represents a challenge in organic synthesis. By means acceptorless dehydrogenative condensation, heterocycles, such indoles, can be obtained. Herein we present an experimental theoretical study this purpose employing heterogeneous catalysts Pt/Al2O3 ZnO combination with acid catalyst (p-TSA) NMP solvent. Under our optimized conditions, diol excess has been reduced down to 2 equivalents. This major advance, allows other diols. 2,3-Butanediol or 1,2-cyclohexanediol employed affording 2,3-dimethyl tetrahydrocarbazoles. In addition, 1,3-propanediol prepare quinolines natural synthetic julolidines.

Language: Английский

Citations

14