Acid-catalyzed synthesis of functionalized arylthio cyclopropane carbaldehydes and ketones

2018 ◽  
Vol 54 (96) ◽  
pp. 13547-13550 ◽  
Author(s):  
Stefania Porcu ◽  
Alberto Luridiana ◽  
Alberto Martis ◽  
Angelo Frongia ◽  
Giorgia Sarais ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
General Strategy ◽  
Reaction Sequence ◽  
Ring Contraction ◽  
Acid Catalyzed ◽  
High Yields ◽  
Ring Contraction Reaction

A general strategy for the synthesis of arylthio cyclopropyl carbaldehydes and ketones via acid catalysed arylthiol addition/ring contraction reaction sequence has been exploited. The procedure led to a wide panel of cyclopropyl carbonyl compounds in high yields and broad substrate scope.

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3263-3271
Author(s):  
Andrey V. Smolobochkin ◽  
Almir S. Gazizov ◽  
Nazerke K. Otegen ◽  
Julia K. Voronina ◽  
Anna G. Strelnik ◽  
...  
Keyword(s):  
Substitution Reaction ◽  
Electrophilic Substitution ◽  
Biologically Active ◽  
Electrophilic Substitution Reaction ◽  
Reaction Sequence ◽  
Active Compounds ◽  
Acid Catalyzed ◽  
High Yields ◽  
Nucleophilic Cyclization ◽  
Mechanism Of The Reaction

Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

scholarly journals A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones

Synthesis ◽  
2020 ◽  
Author(s):  
Francesco Secci ◽  
Stefania Porcu ◽  
Carla Aira Rodriguez ◽  
Angelo Frongia
Keyword(s):  
Nucleophilic Addition ◽  
General Strategy ◽  
Indole Derivatives ◽  
Bronsted Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Brönsted Acid ◽  
Wide Range ◽  
Acid Catalyzed ◽  
High Yields

AbstractA general strategy for the synthesis of indolyl cyclobutanones via a tandem Brønsted acid catalyzed 2-hydroxycyclobutanone activation–indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.

An Efficient Imine Photocyclization as an Alternative to the Pictet-Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes

2020 ◽  
Author(s):  
Antoine Goujon ◽  
Lou Rocard ◽  
Thomas Cauchy ◽  
Piétrick Hudhomme
Keyword(s):  
Solar Cells ◽  
Visible Light ◽  
Organic Solar Cells ◽  
Reaction Sequence ◽  
Large Scope ◽  
High Yields

AzaBenzannulated PDI (AzaBPDI) dyes were synthesized in high yields via a new reaction sequence involving an imine condensation followed by visible light-induced photocyclization. The large scope and efficiency of this alternative to the Pictet-Spengler reaction is demonstrated, and allows the easy preparation of dimeric AzaBPDI as potential non-fullerene acceptors for organic solar cells.

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

2021 ◽  
Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Diazoacetate ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

scholarly journals Copper(I) Chloride/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds

1999 ◽  
Vol 23 (7) ◽  
pp. 434-435
Author(s):  
Mohammed M. Hashemi ◽  
Yousef Ahmadi Beni
Keyword(s):  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Aldehydes And Ketones ◽  
High Yields

Copper(I) Chloride adsorbed on Kieselguhr in the presence of oxygen catalyses oxidation of alkyl halides and alkyl tosylates to the aldehydes and ketones in high yields.

Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung ◽  
2012 ◽  
Vol 66 (3) ◽  
Author(s):  
Takumi Shiraishi ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Carbonyl Compounds ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Bulk Electrolysis ◽  
Lignin Model ◽  
Dimeric Compound ◽  
High Yields ◽  
Short Time

Abstract The direct anodic oxidation of non-phenolic lignin model compounds was investigated to understand their basic behaviors. The results of cyclic voltammetry (CV) studies of monomeric model, such as 1-(4-ethoxy-3-methoxyphenyl)ethanol, are interpreted as the oxidation for Cα-carbonylation did not proceed in the reaction without a catalyst, but a base promotes this reaction. Indeed, the bulk electrolyses of the monomeric lignin model compounds with 2,6-lutidine afforded the corresponding Cα-carbonyl compounds in high yields (60–80%). It is suggested that deprotonation at Cα-H in the ECEC mechanism (E=electron transfer and C=chemical step) is important for Cα-carbonylation. In the uncatalyzed bulk electrolysis of a β-O-4 model dimeric compound, 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether, the corresponding Cα-carbonyl compound was not detected but as a result of Cα-Cβcleavage 4-O-ethylvanillin was found in 40% yield. In the electrolysis reaction in the presence of 2,6-lutidine (as a sterically hindered light base), the reaction stopped for a short time unexpectedly. These results indicate the different electrochemical behavior of simple monomeric model compounds and dimeric β-O-4 models. The conclusion is that direct electrooxidation is unsuitable for Cα-carbonylation of lignin.

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

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