scholarly journals Metal-Free α-C(sp3)–H Functionalized Oxidative Cyclization of Tertiary N,N-Diaryl Amino Alcohols: Theoretical Approach for Mechanistic Pathway

Molecules ◽  
2017 ◽  
Vol 22 (4) ◽  
pp. 547 ◽  
Author(s):  
Zakir Ullah ◽  
Mihyun Kim
Keyword(s):  
Theoretical Approach ◽  
Amino Alcohols ◽  
Oxidative Cyclization ◽  
Metal Free ◽  
Mechanistic Pathway

scholarly journals Metal-Free α-C(sp3)–H Functionalized Oxidative Cyclization of Tertiary N,N-Diaryl Amino Alcohols: Theoretical Approach for Mechanistic Pathway

2017 ◽  
Author(s):  
Zakir Ullah ◽  
Mihyun Kim
Keyword(s):  
Free Energy ◽  
Radical Cation ◽  
Theoretical Approach ◽  
Dft Calculation ◽  
Amino Alcohols ◽  
Oxidative Cyclization ◽  
Solution Phase ◽  
Ionic Mechanism ◽  
Metal Free ◽  
Mechanistic Pathway

The mechanistic pathway of TEMPO/I2-mediated oxidative cyclization of N,N-diaryl amino alcohols 1 is investigated in this study. Based on our direct empirical experiments, three key intermediates (the aminium radical cation 3, the α-aminoalkyl radical 4, and the iminium 5), four kind reactive species (radical TEMPO, cationic TEMPO, TEMPO-I and iodo radical) and three kind pathways (1. SET/PCET mechanism, 2. HAT/1,6-H transfer mechanism, 3. Ionic mechanism) were assumed. Under the assumption, nine free energy diagrams are acquired through DFT calculation. From the comparison of the solution phase free energy, some possibility can be excluded and then the chosen plausible mechanisms are concretized with the more stable intermediate 7.

Metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes: a facile access to 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles

2021 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Zhengkai Chen ◽  
Jiajun Zhang ◽  
Tian-Hui Xu
Keyword(s):  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Metal Free

A metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes for the efficient synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles has been developed. Notable features of this protocol include readily accessible starting materials, a broad substrate...

ChemInform Abstract: I2Promoted Domino Oxidative Cyclization for One-Pot Synthesis of 2-Acylbenzothiazoles via Metal-Free sp3C-H Functionalization.

ChemInform ◽  
2012 ◽  
Vol 43 (52) ◽  
pp. no-no
Author(s):  
Yan-Ping Zhu ◽  
Mi Lian ◽  
Feng-Cheng Jia ◽  
Mei-Cai Liu ◽  
Jing-Jing Yuan ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis

Electrochemical Oxidative Cyclization of Alkenes, Boronic Acids, and Dichalcogenides to Access Chalcogenated Boronic Esters and 1,3-Diols

2021 ◽  
Author(s):  
Changfeng Huang ◽  
Jijing Hu ◽  
Guangxian Chen ◽  
Minjian Wu ◽  
Hua Cao ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Oxidative Cyclization ◽  
Environmentally Benign ◽  
Allylic Alcohols ◽  
Efficient Manner ◽  
Metal Free ◽  
Boronic Esters

A sustainable, environmentally benign electrochemical oxidative three-component cyclization of allylic alcohols, boronic acids, and dichalcogenides under metal-free and oxidant-free conditions has been developed, which provides an efficient manner for the...

Metal-free cyclization of unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines

2019 ◽  
Vol 55 (61) ◽  
pp. 8943-8946 ◽  
Author(s):  
Xiaobing Liu ◽  
Yao Zhou ◽  
Qiuling Song
Keyword(s):  
Oxidative Cyclization ◽  
Metal Free

An oxidative cyclization of β,γ-unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines under metal-free conditions is presented.

ChemInform Abstract: Synthesis of 6-Substituted Phenanthridines by Metal-Free, Visible-Light Induced Aerobic Oxidative Cyclization of 2-Isocyanobiphenyls with Hydrazines.

ChemInform ◽  
2014 ◽  
Vol 45 (36) ◽  
pp. no-no
Author(s):  
Tiebo Xiao ◽  
Linyong Li ◽  
Guoliang Lin ◽  
Qile Wang ◽  
Ping Zhang ◽  
...  
Keyword(s):  
Visible Light ◽  
Oxidative Cyclization ◽  
Metal Free

Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 912-917 ◽  
Author(s):  
Parviz Ranjbar ◽  
Narjes Rezaei ◽  
Ehsan Sheikhi
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Benzylic Alcohols ◽  
Metal Free ◽  
Novel Synthesis

A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

Sign in / Sign up

Export Citation Format

Share Document