Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.

ABSTRACT: A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating ?-(het)aroyl-?-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular O-arylation, furnishing the 2-(het)aryl/alkyl-3-cyanobenzofurans in high yields. A probable mechanism for the base-induced cleavage of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles to ?-(het)aroyl-?-(2-bromoaryl)acetonitriles in the presence of benzyl carbamate has been proposed.

SUBMITTER: Saraiah B

PROVIDER: S-EPMC6644376 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.

Saraiah Bonagiri B Gautam Vibha V Acharya Anand A Pasha Mohamed Afzal MA Ila Hiriyakkanavar H

ACS omega 20180726 7

A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating α-(het)aroyl-α-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular <i>O</i>-arylation, furnishing the 2-(het)aryl/alkyl-3-cyanobenzofurans in high yields. A probable mechanism for the base-induced cleavage of 2-(2-bromoaryl)-3-(het)aryl ...[more]

PMID: 31458967

Similar Datasets

One-Pot Synthesis of α-Alkyl Styrene Derivatives.

Project description:There is a significant need to develop more rapid and efficient routes to styrene derivatives, since they are extensively used in polymer sciences. This manuscript reports a one-pot synthesis of an array of α-alkyl styrene derivatives from readily available natural products (i.e., estragole and safrole). This method is regioselective, producing a rearranged adduct, under transition metal-free conditions. This methodology has broad nucleophile scope, even tolerating sterically hindered nucleophiles; it is general for carbon, nitrogen, oxygen, and sulfur nucleophiles.

| S-EPMC8359136 | biostudies-literature

An efficient three-component, one-pot synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines in water.

Project description:A convenient and practical method for the synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines has been developed via a three-component, one-pot reaction from aldehydes, malononitrile and S-alkylisothiouronium salts in water at room temperature. A series of polysubstituted pyrimidines were prepared by this method in moderate to excellent yields. In addition, two kinds of pyrimidine-fused heterocyclic derivatives with potential pharmacological activity were constructed from our 2-alkylthio-4-amino-5-cyano-6-arylpyrimidines.

| S-EPMC7088670 | biostudies-literature

One-pot synthesis of epoxides from benzyl alcohols and aldehydes.

Project description:A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey-Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

| S-EPMC6142752 | biostudies-literature

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.

Project description:A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.

| S-EPMC5369543 | biostudies-literature

One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation.

Project description:The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl)aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-chlorination/aryne annulation or Ac(2)O-acylation/deprotection/aromatization protocols.

| S-EPMC3764999 | biostudies-literature

Pot economy and one-pot synthesis.

Project description:The one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry. In this review, the characteristics and limitations of various one-pot syntheses of biologically active molecules are explained, primarily involving organocatalytic methods as key tactics. Besides catalysis, the pot-economy concepts presented herein are also applicable to organometallic and organic reaction methods in general.

| S-EPMC5529999 | biostudies-other

Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.

Project description:A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor-acceptor cyclopropane family, has been developed. This method, based on the Corey-Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.

| S-EPMC7729819 | biostudies-literature

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone.

Project description:A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.

| S-EPMC5288754 | biostudies-literature

One-Pot Multicomponent Coupling Reaction of Catechols, Benzyl Alcohols/Benzyl Methyl Ethers, and Ammonium Acetate toward Synthesis of Benzoxazoles.

Project description:The multicomponent coupling reaction of catechol, ammonium acetate, and benzyl alcohol/benzyl methyl ether in the presence of a Fe(III) catalyst precursor afforded benzoxazole derivatives in good to excellent yields. The notable features of this protocol are abundant availability of the catalyst system, large-scale synthesis, high diversity, and high yields of products.

| S-EPMC8412954 | biostudies-literature

One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent.

Project description:The reaction of 5,10,15-tritolylcorrole with EtMgBr opens the way for novel functionalizations of the corrole ring. DDQ oxidation of the macrocycle, followed by addition of the Grignard reagent, led to the formation of 5- and 10-alkyl substituted isocorroles in satisfying yields. Together with the one-pot formation of these isocorrole isomers, the use of such a nucleophile evidenced the competitive reactivity of the macrocycle ?-positions, leading to the formation of 2-bromo- and 3-bromo-5,10,15-tritolylcorrole. While the formation of these monobromocorrole derivatives is not unprecedented, this is the first time the isomers have been separated and fully characterized. Furthermore, the higher yields of the 2-substituted species highlight a useful regioselectivity for the substitution reaction.

| S-EPMC3002075 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data