scholarly journals Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

2015 ◽  
Vol 11 ◽  
pp. 66-73 ◽  
Author(s):  
Bianca Rossi ◽  
Nadia Pastori ◽  
Simona Prosperini ◽  
Carlo Punta
Keyword(s):  
Free Radical ◽  
Cyclic Ether ◽  
Radical Addition ◽  
Domino Reaction ◽  
Alcohol Molecule ◽  
Secondary Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions

Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary β-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing the formation of secondary products. The secondary products are possibly derived from a competitive domino reaction, which involves further oxidation of the ketyl radicals.

Free-Radical Addition to Ketimines Generated In Situ. New One-Pot Synthesis of Quaternary α-Aminoamides Promoted by a H2O2/TiCl4−Zn/HCONH2System

2010 ◽  
Vol 12 (17) ◽  
pp. 3898-3901 ◽  
Author(s):  
Nadia Pastori ◽  
Cosimina Greco ◽  
Angelo Clerici ◽  
Carlo Punta ◽  
Ombretta Porta
Keyword(s):  
Free Radical ◽  
Radical Addition ◽  
One Pot ◽  
One Pot Synthesis ◽  
Free Radical Addition

ChemInform Abstract: Free-Radical Addition to Ketimines Generated in situ. New One-Pot Synthesis of Quaternary α-Aminoamides Promoted by a H2O2/TiCl4-Zn/HCONH2 System.

ChemInform ◽  
2010 ◽  
Vol 41 (51) ◽  
pp. no-no
Author(s):  
Nadia Pastori ◽  
Cosimina Greco ◽  
Angelo Clerici ◽  
Carlo Punta ◽  
Ombretta Porta
Keyword(s):  
Free Radical ◽  
Radical Addition ◽  
One Pot ◽  
One Pot Synthesis ◽  
Free Radical Addition

Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction of o-alkenyl aromatic isocyanides with diazo compounds

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinazoline Derivatives

Various o-alkenyl aromatic isocyanides were prepared from readily available reactants for their double annulation with diazo compounds for a one-pot synthesis of pyrazolo[1,5-c]quinazolines under mild reaction conditions.

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

A new approach to arylhydrazides via the reaction of the Mitsunobu reagent with arynes: further application to access diverse nitrogen-containing heterocycles in one pot

2017 ◽  
Vol 4 (8) ◽  
pp. 1636-1639 ◽  
Author(s):  
Bin Cheng ◽  
Bian Bao ◽  
Yanhe Chen ◽  
Ning Wang ◽  
Yun Li ◽  
...  
Keyword(s):  
One Pot ◽  
New Approach ◽  
Mild Conditions ◽  
Highly Active ◽  
Active Intermediates

A new route to arylhydrazides involving the reaction of two highly active intermediates, the 1,3-zwitterion generated in situ from the Mitsunobu reagent and arynes, under mild conditions has been developed.

Ligand free copper(i)-catalyzed synthesis of diaryl ether with Cs2CO3via a free radical path

2015 ◽  
Vol 44 (27) ◽  
pp. 12086-12090 ◽  
Author(s):  
Hong-Jie Chen ◽  
Mei-Chun Tseng ◽  
I-Jui Hsu ◽  
Wei-Ting Chen ◽  
Chien-Chung Han ◽  
...  
Keyword(s):  
Free Radical ◽  
Catalytic Reaction ◽  
Coupling Reaction ◽  
Reaction Conditions ◽  
Esi Ms ◽  
Ms Analysis ◽  
Diaryl Ether ◽  
Ligand Free

Complexes [Cu(i)(2,4-dimethylphenoxy)2]− (A) and [Cu(ii)(2,4-dimethylphenoxy)2(p-tolyl)]− (B) were observed by in situ ESI-MS analysis of the ligand free copper(i)-catalyzed C–O coupling reaction using Cs2CO3 under the catalytic reaction conditions.

scholarly journals Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

2013 ◽  
Vol 9 ◽  
pp. 974-982 ◽  
Author(s):  
Tamashree Ghosh ◽  
Abhishek Santra ◽  
Anup Kumar Misra
Keyword(s):  
Reaction Sequence ◽  
Reaction Conditions ◽  
One Pot ◽  
Carbon Tetrabromide

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

scholarly journals Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

2017 ◽  
Vol 13 ◽  
pp. 2023-2027 ◽  
Author(s):  
Hao Wang ◽  
Cui Chen ◽  
Weibing Liu ◽  
Zhibo Zhu
Keyword(s):  
Room Temperature ◽  
Synthetic Methods ◽  
Chemical Modifications ◽  
One Pot ◽  
Butyl Hydroperoxide ◽  
Radical Intermediates ◽  
Mild Conditions ◽  
Tert Butyl Hydroperoxide ◽  
Potential Applications

We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential applications and allow further chemical modifications, enabling the preparation of synthetically valuable molecules.

scholarly journals A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis- N -heterocycles: rationalization by electronic structure calculations

2018 ◽  
Vol 5 (9) ◽  
pp. 181140 ◽  
Author(s):  
Liliana Damas ◽  
Rui M. B. Carrilho ◽  
Sandra C. C. Nunes ◽  
Alberto A. C. C. Pais ◽  
László Kollár ◽  
...  
Keyword(s):  
Electronic Structure ◽  
Electronic Structure Calculations ◽  
Reaction Conditions ◽  
One Pot ◽  
New Family ◽  
Synthetic Strategy ◽  
Heterocyclic Derivatives ◽  
Amine Groups ◽  
Structure Calculations

An unprecedented palladium-catalysed sequential aminocarbonylation/cyclization synthetic strategy, using carbon monoxide and structurally different aliphatic diamines as N -nucleophiles, gives access, in one pot, to a new family of indole-based N -heterocyclic derivatives (hydropyrazinones, benzodiazepinones and hydroquinoxalines). Optimization of the reaction conditions towards double carbonylation ( P CO = 30 bar, T = 80°C, iodoindole/diamine ratio = 1 : 1.5, toluene as solvent) allowed the target cyclic products, which are formed in situ via intramolecular cyclization of the ketocarboxamide intermediates, to be obtained through a nucleophilic addition/elimination reaction with the pendant terminal amine groups. The structure of the diamine nucleophile was revealed to affect the reaction's selectivity, with the best yields for the cyclic products being obtained in the presence of (1 S , 2S )-(+)-cyclohexane-1,2-diamine ( a ) as the nucleophile, using either 5- or 7-iodoindole as the substrate. The reaction's selectivity was rationalized based on electronic structure calculations, which explain the effect of the diamine structure on the predominant formation of the cyclic products.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1437-1441
Author(s):  
Xu yan Cao ◽  
Fei Huang ◽  
Songlin Zhang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Mild Conditions ◽  
Allyl Halides ◽  
Barbier Reaction

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

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