scholarly journals Trichloroacetamidate Triggered Expeditious and Novel Synthesis of N-Acylbenzotriazoles

SynOpen ◽  
2021 ◽  
Author(s):  
Vinod K Tiwari ◽  
MANGAL SINGH YADAV ◽  
Manoj K Jaiswal ◽  
Sunil Kumar
Keyword(s):  
Carboxylic Acids ◽  
Easy Access ◽  
One Pot ◽  
Diverse Range ◽  
Free Condition ◽  
Metal Free ◽  
Activation Pathway ◽  
Novel Synthesis ◽  
Facile Route

A facile route for the synthesis of diverse range of N-acylbenzotriazole derivatives from corresponding carboxylic acids has been established through carbonyl activation pathway. In this method, trichloroacetonitrile is performed as an effective reagent for an easy access of N-acylbenzotriazoles which was simply proceed through the activation of carboxylic acids via in situ imidate formation in anhydrous 1,2 dichloroethane followed by addition of 1H-benzotriazole at 80 oC for 3-4 hours. Easy handling, one-pot, and metal-free condition demonstrate the notable merits of the devised protocol.

N-Acylbenzotriazole as Proficient Substrate for an Easy Access of Urea, Acyl urea, Carbamates and Thiocarbamates via Curtius Rearrangement Using DPPA as Azide Donor

Synthesis ◽  
2021 ◽  
Author(s):  
MANGAL SINGH YADAV ◽  
SUMIT KUMAR SINGH ◽  
Anand K Agrihari ◽  
Anoop S Singh ◽  
Vinod K Tiwari
Keyword(s):  
Column Chromatography ◽  
Anhydrous Toluene ◽  
Easy Access ◽  
One Pot ◽  
Diverse Range ◽  
Curtius Rearrangement ◽  
Free Condition ◽  
Metal Free ◽  
High Reaction ◽  
Curtius Degradation

A diverse range of urea, N-acyl urea, and thiocarbamates has been synthesized in good to excellent yields by reacting N-acylbenzotriazoles individually with amines or amides or thiols or phenols in presence of diphenylphosphorylazide (DPPA) as a suitable azide donor in anhydrous toluene at 110 oC for 3-4 hours. In this route, DPPA is found to be a well alternative of trimethylsilylazide and NaN3 for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free condition, straight-forward nature, easy to handling, use of readily available reagents, and in many cases avoid of the column chromatography are the notable features of the devised protocol.

One-pot synthesis of bio-based polycarbonates from dimethyl carbonate and isosorbide under metal-free condition

2020 ◽  
Vol 22 (14) ◽  
pp. 4550-4560
Author(s):  
Wenjuan Fang ◽  
Zhencai Zhang ◽  
Zifeng Yang ◽  
Yaqin Zhang ◽  
Fei Xu ◽  
...  
Keyword(s):  
Dimethyl Carbonate ◽  
One Pot ◽  
Free Condition ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Synthetic Strategy

A synthetic strategy for bio-based polycarbonate was developed via one-pot polymerization of renewable monomer isosorbide and dimethyl carbonate using eco-friendly organo-catalysts.

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.

One-pot construction of sterically challenging and diverse polyarylphenols via transition-metal-free benzannulation and their potent in vitro antioxidant activity

2017 ◽  
Vol 15 (9) ◽  
pp. 2052-2062 ◽  
Author(s):  
Shizuka Mei Bautista Maezono ◽  
Tej Narayan Poudel ◽  
Yong Rok Lee
Keyword(s):  
Antioxidant Activity ◽  
Transition Metal ◽  
Antioxidant Activities ◽  
One Pot ◽  
Metal Free ◽  
Novel Synthesis ◽  
In Vitro Antioxidant Activity

One pot novel synthesis of highly functionalized polyarylphenols via benzannulation under transition-metal-free conditions and their antioxidant activities are described.

Formal α-trifluoromethylthiolation of carboxylic acid derivatives via N-acyl pyrazoles

2020 ◽  
Vol 56 (20) ◽  
pp. 3073-3076 ◽  
Author(s):  
Francesca Franco ◽  
Sara Meninno ◽  
Maurizio Benaglia ◽  
Alessandra Lattanzi
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
One Pot ◽  
Metal Free

A direct and general one-pot approach to α-trifluoromethylthiolated amides, esters and carboxylic acids has been successfully developed under mild, catalytic and metal-free conditions.

One-Pot Synthesis of 2-Substituted Benzoxazoles Directly from Carboxylic Acids

2008 ◽  
Vol 61 (11) ◽  
pp. 881 ◽  
Author(s):  
Dinesh Kumar ◽  
Santosh Rudrawar ◽  
Asit K. Chakraborti
Keyword(s):  
Carboxylic Acids ◽  
Methanesulfonic Acid ◽  
Acid Chlorides ◽  
Double Bonds ◽  
Reaction Conditions ◽  
One Pot ◽  
Effective Catalyst ◽  
One Pot Synthesis ◽  
Highly Effective

Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.

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