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, 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.

Transition Metal-free Approach for the Synthesis of 2-substituted Quinazolin-4(3H)-one via Anhydrous Magnesium Perchlorate

2020 ◽  
Vol 7 (2) ◽  
pp. 118-123
Author(s):  
Shweta Mishra ◽  
Debashree Das ◽  
Adarsh Sahu ◽  
Shailendra Patil ◽  
Ram Kishor Agarwal ◽  
...  
Keyword(s):  
Transition Metal ◽  
Aromatic Aldehydes ◽  
Magnesium Perchlorate ◽  
Reaction Conditions ◽  
Metal Free ◽  
Convenient Synthesis ◽  
Wide Availability ◽  
Ic50 Values ◽  
Antileishmanial Activities ◽  
Green Conditions

Background: A convenient and efficient methodology for the synthesis of quinazolin- 4(3H)-ones from simple and readily available 2-amino benzamides and aromatic aldehydes in ethanol using Magnesium perchlorate are being reported in the present study. Good to excellent isolated yields (68-95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The affordability of the catalyst, the wide availability of the starting materials, transition metal free synthesis and the simplicity of the procedure renders the present methodology useful in organic synthesis. Objective: A maneuver methodology developed for the synthesis of quinazolin-4(3H)-ones via using Magnesium perchlorate from 2-amino benzamides and aromatic aldehydes in ethanol. Methods: 10% mol anhydrous Magnesium perchlorate in presence of ethanol give to simply rapid formation of Quinazolin-4(3H)-ones from 1 mole of 2-amino benzamides and 1 mole of aromatic aldehydes. Results: Screening results of Anti-leishmanial showed that out of the synthesized series of 12 compounds, compounds 3c, 3d, 3g, 3h and 3i showed significant antileishmanial activities (L. donavani) with IC50 values 8.39, 9.37, 9.43, 7.1 and 8.7 μM. Conclusion: In summary, we have developed convenient synthesis of quinazolin-4(3H)-one, from simple and easily available precursor employing anhydrous Mg(ClO4)2 under green conditions.

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 oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls

2015 ◽  
Vol 51 (27) ◽  
pp. 5925-5928 ◽  
Author(s):  
Ren-Jin Tang ◽  
Qing He ◽  
Luo Yang
Keyword(s):  
Aromatic Aldehydes ◽  
Direct Access ◽  
Metal Free ◽  
First Time ◽  
Biaryl Compounds

A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds 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...

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.

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