One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3221-3230 ◽  
Author(s):  
Wei Sun ◽  
Mingjuan Zhang ◽  
Peilang Li ◽  
Yiqun Li
Keyword(s):  
Catalytic System ◽  
Multicomponent Reaction ◽  
Functional Group ◽  
Cascade Process ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
System A

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.

Fe(III)/l-Valine-Catalyzed One-Pot Synthesis of N-Sulfinyl- and N-Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1232-1238
Author(s):  
Guofu Zhang ◽  
Yunzhe Xing ◽  
Shengjun Xu ◽  
Chengrong Ding ◽  
Shang Shan
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Cascade Reaction ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Oxidation Of Alcohols

An efficient Fe(III), l-valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N-sulfinyl- and N-sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.

Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4170-4182 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Ya-Ting Li ◽  
Ting Gao ◽  
Sha-Sha Guo ◽  
Bei Yang ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Functional Group ◽  
High Efficiency ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Ligand Free ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and regioselectivity, easy operation, and ligand-free CuI.

scholarly journals One-Pot Reductive Acetylation of Aldehydes using 1-Hydrosilatrane in Acetic Acid

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 1-3 ◽  
Author(s):  
Reuben James ◽  
Sharon Herlugson ◽  
Sami Varjosaari ◽  
Vladislav Skrypai ◽  
Zainab Shakeel ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Functional Group ◽  
Building Blocks ◽  
Flash Chromatography ◽  
Primary Alcohols ◽  
Facile Synthesis ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions

A one-pot, direct reductive acetylation of aldehydes was achieved under mild conditions using 1-hydrosilatrane as a safe and easily accessible catalyst. Described herein is a facile synthesis that produces acylated primary alcohols that can serve as valuable building blocks for organic synthesis. The method has good functional group tolerance and works for a range of aryl aldehydes, with the notable exception of electron-rich arenes. A library of esters was isolated by flash chromatography in yields as high as 92%.

scholarly journals I2-SDS-H2O System: A highly Efficient Dual Catalytic Green System for Deprotection of Imines and in Situ Preparation of Bis(indolyl)alkanes from Indoles in Water

2012 ◽  
Vol 2012 ◽  
pp. 1-6
Author(s):  
Parasa Hazarika ◽  
Pallab Pahari ◽  
Manash Jyoti Borah ◽  
Dilip Konwar
Keyword(s):  
Catalytic System ◽  
Room Temperature ◽  
One Pot ◽  
Highly Efficient ◽  
In Situ Preparation ◽  
System A ◽  
Neutral Conditions ◽  
Green System

A novel catalytic system consisting of I2-SDS-H2O has been developed which cleaves 2,3-diaza-1,3-butadiene, 1-aza-1,3-butadienes, oximes and in presence of indoles in the medium uses the corresponding aldehyde products to produce bis(indolyl)alkanes in situ. This one pot simple and mild dual catalytic system works in water at room temperature under neutral conditions.

An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions

2015 ◽  
Vol 39 (12) ◽  
pp. 9693-9699 ◽  
Author(s):  
S. Nagarajan ◽  
Tanveer Mahamadali Shaikh ◽  
Elango Kandasamy
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Functional Group ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Synthetic Utility

This article describes an efficient protocol for the syntheses of 2,3-dihydroquinazolinones. The synthetic utility of this methodology has been demonstrated with 30 different substrates. The reaction showed good functional group tolerance and high levels of catalytic activity.

scholarly journals Vanadium(V) Complex-Catalyzed One-Pot Synthesis of Phenanthridines via a Pictet-Spengler-Dehydrogenative Aromatization Sequence

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 860
Author(s):  
Makoto Sako ◽  
Romain Losa ◽  
Tomohiro Takiishi ◽  
Giang Vo-Thanh ◽  
Shinobu Takizawa ◽  
...  
Keyword(s):  
Functional Materials ◽  
Biologically Active ◽  
Acid Catalysts ◽  
Lewis Acid Catalysts ◽  
One Pot ◽  
Sequential Reaction ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Aromatization Reaction

Phenanthridine and its derivatives are important structural motifs that exist in natural products, biologically active compounds, and functional materials. Here, we report a mild, one-pot synthesis of 6-arylphenanthridine derivatives by a sequential cascade Pictet-Spengler-dehydrogenative aromatization reaction mediated by oxovanadium(V) complexes under aerobic conditions. The reaction of 2-(3,5-dimethoxyphenyl)aniline with a range of commercially available aryl aldehydes provided the desired phenanthridine derivatives in up to 96% yield. The ability of vanadium(V) complexes to function as efficient redox and Lewis acid catalysts enables the sequential reaction to occur under mild conditions.

scholarly journals One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

2016 ◽  
Vol 12 ◽  
pp. 1487-1492 ◽  
Author(s):  
Bo Yang ◽  
Chuanye Tao ◽  
Taofeng Shao ◽  
Jianxian Gong ◽  
Chao Che
Keyword(s):  
Functional Group ◽  
Nucleophilic Reaction ◽  
One Pot ◽  
Ene Reaction ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Three Component Coupling

A novel three-component reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo[1,2-a]pyridines in a one-pot fashion utilizing readily available 2-aminopyridines, isatins and isocyanides. The three-component coupling proceeds through the Groebke–Blackburn–Bienaymé reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group.

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