Unravelling 2-aminoquinazolin-4(3H)-one as an organocatalyst for the chemoselective reduction of nitroarenes

2018 ◽  
Vol 42 (2) ◽  
pp. 1373-1378 ◽  
Author(s):  
Maheshwar S. Thakur ◽  
Onkar S. Nayal ◽  
Rohit Rana ◽  
Manoranjan Kumar ◽  
Sushila Sharma ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Transition Metal ◽  
Hydrazine Hydrate ◽  
Metal Free ◽  
First Time

A novel, green and transition metal-free reduction of nitroarenes has been explored. 2-Aminoquinazolin-4(3H)-one and its derivatives have been first time investigated as hydrogen bonding organocatalysts for the activation of hydrazine hydrate to reduce nitroarenes.

Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2395-2409
Author(s):  
Weiwei Qin ◽  
Zhaodong Li ◽  
Yiming Du ◽  
Yue Chen ◽  
Yun-Lin Liu
Keyword(s):  
Transition Metal ◽  
Magnaporthe Grisea ◽  
Single Step ◽  
Domino Reaction ◽  
Efficient Synthesis ◽  
Metal Free ◽  
Efficient Access ◽  
First Time ◽  
Antibacterial Evaluation ◽  
Addition Pathway

An efficient, PhI(OAc)2-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.

The peroxodisulfate-assisted three-component benzylation of coumarins with styrenes and KSCN: A transition-metal-free approach for the synthesis of 3-(1-aryl-2-thiocyanatoethyl)-2H-chromen-2-one in ethyl lactate

2021 ◽  
Author(s):  
Palani Natarajan ◽  
Priya ◽  
Deachen Chuskit
Keyword(s):  
Transition Metal ◽  
Ethyl Lactate ◽  
Metal Free ◽  
Reaction Proceeds ◽  
First Time

The peroxodisulfate-assisted three-component benzylation of coumarins with styrenes and KSCN to 3-(1-aryl-2-thiocyanatoethyl)-2H-chromen-2-one is reported for the first time. This reaction proceeds via the consecutive addition of SCN radical to styrenes...

Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and 3-alkyl indolizines

2017 ◽  
Vol 15 (23) ◽  
pp. 5016-5024 ◽  
Author(s):  
Yan Liu ◽  
Huayou Hu ◽  
Junyu Zhou ◽  
Wenhui Wang ◽  
Youliang He ◽  
...  
Keyword(s):  
Transition Metal ◽  
Halogenated Hydrocarbons ◽  
Tandem Reaction ◽  
Synthetic Route ◽  
Metal Free ◽  
First Time

A transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons is reported for the first time using a tandem reaction.

Metal-free enantioselective addition of nucleophilic silicon to aromatic aldehydes catalyzed by a [2.2]paracyclophane-based N-heterocyclic carbene catalyst

2017 ◽  
Vol 15 (15) ◽  
pp. 3202-3206 ◽  
Author(s):  
Ping An ◽  
Yuwen Huo ◽  
Zhen Chen ◽  
Chun Song ◽  
Yudao Ma
Keyword(s):  
Transition Metal ◽  
Aromatic Aldehydes ◽  
Metal Free ◽  
Enantioselective Addition ◽  
First Time

A transition metal-free enantioselective 1,2-silylation of aromatic aldehydes to yield chiral α-hydroxysilanes was developed for the first time.

Transition-metal-free α-arylation of nitroketones with diaryliodonium salts for the synthesis of tertiary α-aryl, α-nitro ketones

2019 ◽  
Vol 55 (1) ◽  
pp. 119-122 ◽  
Author(s):  
Yang An ◽  
Xiao-Ming Zhang ◽  
Ze-Yu Li ◽  
Wen-Hui Xiong ◽  
Run-Dong Yu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
First Time

Transition-metal-free α-arylation of α-nitroketones with diaryliodonium salts has been developed for the first time and applied in the synthesis of tiletamine.

Transition-metal-free synthesis of 1,1-diboronate esters with a fully substituted benzylic center via diborylation of lithiated carbamates

2017 ◽  
Vol 15 (16) ◽  
pp. 3418-3422 ◽  
Author(s):  
Haonan Zhao ◽  
Min Tong ◽  
Haijun Wang ◽  
Senmiao Xu
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
First Time

Diborylation of lithiated carbamates is reported for the first time to synthesize 1,1-diboronate esters with a fully substituted benzylic center.

Transition-metal-free Decarbonylative Alkylation of N-Aryl a-Hydroxy Amides via Triple C–C Bond Cleavages and Their Selective Deuteration

2021 ◽  
Author(s):  
Chengyu Sun ◽  
Yang Yu ◽  
Xiao Zhang ◽  
Yonghai Liu ◽  
Chengtao Sun ◽  
...  
Keyword(s):  
Transition Metal ◽  
Alkylation Reaction ◽  
Metal Free ◽  
Selective Deuteration ◽  
First Time

We disclose a transition-metal-free decarbonylative alkylation reaction for the synthesis of N-aryl a-hydroxy amides via precise cleavages and reorganizations of three C–C s bonds. For the first time, the medium-sized...

Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

2017 ◽  
Vol 19 (11) ◽  
pp. 2541-2545 ◽  
Author(s):  
Palaniraja Subramaniam ◽  
Chandrasekaran Ramasubbu ◽  
Selvaraj Athiramu
Keyword(s):  
Hydrogen Bonding ◽  
Transition Metal ◽  
High Purity ◽  
Intramolecular Hydrogen Bonding ◽  
Chromatographic Purification ◽  
Metal Free ◽  
Intramolecular Hydrogen ◽  
High Stereoselectivity ◽  
Column Chromatographic

An intramolecular hydrogen bonding directed highly stereospecific, transition metal free synthetic protocol for amide substituted β-aminoenones. High stereoselectivity, excellent yields and high purity were achieved by mere filtration without column chromatographic purification.

scholarly journals Transition Metal-Free Intramolecular Friedel-Crafts Reaction by Alkene Activation: A Method for the Synthesis of Some Novel Xanthene Derivatives

2021 ◽  
Author(s):  
Tülay Yıldız ◽  
İrem Baştaş ◽  
Hatice Başpınar Küçük
Keyword(s):  
Transition Metal ◽  
Trifluoroacetic Acid ◽  
Room Temperature ◽  
Synthesis Method ◽  
Biological Significance ◽  
Metal Free ◽  
New Synthesis ◽  
Starting Point ◽  
Xanthene Derivatives ◽  
First Time

In this work, new derivatives (substituted 9-methyl-9-arylxanthenes) of xanthene compounds (5a-5l) of possible biological significance were synthesized by developing a new synthesis method. In order to obtain xanthene derivatives, the original alkene compounds to be used as the starting point were synthesized in four steps using appropriate reactions. Cyclization reaction by intramolecular Friedel-Crafts alkylation was carried out in order to synthesize the desired xanthene derivatives using the alkenes as starting compounds. Intramolecular Friedel-Crafts reaction was catalyzed by trifluoroacetic acid (TFA) and provided some novel substituted 9-methyl-9-arylxanthenes with good yields at room temperature within 6–24 hours. As a result, an alkene compound was used for activation with TFA in the synthesis of xanthene through intramolecular Friedel-Crafts alkylation for the first time.

scholarly journals Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

2021 ◽  
Vol 17 ◽  
pp. 2203-2208
Author(s):  
Tülay Yıldız ◽  
İrem Baştaş ◽  
Hatice Başpınar Küçük
Keyword(s):  
Transition Metal ◽  
Trifluoroacetic Acid ◽  
Room Temperature ◽  
Synthesis Method ◽  
Biological Significance ◽  
Cyclization Reaction ◽  
Metal Free ◽  
New Synthesis ◽  
Xanthene Derivatives ◽  
First Time

In this work, new derivatives (substituted 9-methyl-9-arylxanthenes) of xanthene compounds (5a–l) of possible biological significance were synthesized by developing a new synthesis method. In order to obtain xanthene derivatives, the original alkene compounds to be used as the starting materials were synthesized in four steps using appropriate reactions. A cyclization reaction by intramolecular Friedel–Crafts alkylation was carried out in order to synthesize the desired xanthene derivatives using the alkenes as starting compounds. The intramolecular Friedel–Crafts reaction was catalyzed by trifluoroacetic acid (TFA) and provided some novel substituted 9-methyl-9-arylxanthenes with good yields at room temperature within 6–24 hours. As a result, an alkene compound was used for activation with TFA in the synthesis of xanthene through intramolecular Friedel–Crafts alkylation for the first time.

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