Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation (original) (raw)

Profile image of Yulia VolkovaYulia Volkova

2012, Tetrahedron Letters

visibility

description

4 pages

link

1 file

Sign up for access to the world's latest research.

checkGet notified about relevant papers

checkSave papers to use in your research

checkJoin the discussion with peers

checkTrack your impact

Spiro Isoxazolines via Nitrile Oxide 1,3-Dipolar Cycloaddition Reactions

Paul Savage

Current Organic Chemistry, 2010

View PDFchevron_right

4-Nitroisoxazoles as nitroalkene heterodienes: diastereoselective synthesis of spiro tricyclic nitroso acetals by thermal reactions with ethyl vinyl ether

Andrea Danesi, Cristina Faggi

Tetrahedron, 2001

AbstractÐA few 4-nitroisoxazoles were found to undergo highly diastereoselective pericyclic homodomino processes with the title enol ether affording 1,6,9-trioxa-5,9a-diazacyclopenta[d]indenes through bicyclic nitronates as key intermediates. Formation of isoxazolo± oxepine systems is also reported together with a domino reaction with the above reagent and methyl acrylate. Two X-ray analyses of compounds 8 and 13 were carried out to ®rmly establish their stereochemistry. q

View PDFchevron_right

Cycloadditions. 45. Annulation of heterocycles via intramolecular nitrile oxide-heterocycle cycloaddition reaction

Alfred Hassner

The Journal of Organic Chemistry, 1991

View PDFchevron_right

Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes

Anup jawalekar

Chemical Communications, 2011

View PDFchevron_right

Electron-deficient isoxazoles: 1,3-dipolar cycloadditions of ethyl 4-nitro-3-phenylisoxazole-5-carboxylate with diazoalkanes

susanna bracci

Journal of Organic Chemistry, 1989

View PDFchevron_right

Isoxazolodihydropyridinones: 1,3-Dipolar Cycloaddition of Nitrile Oxides onto 2,4-Dioxopiperidines

Jerry Dallas

ACS Combinatorial Science, 2012

View PDFchevron_right

Design and Synthesis of 2-Nitroimidazoles with Variable Alkylating and Acylating Functionality

Bill Elliott

Chemical and Pharmaceutical Bulletin, 2014

View PDFchevron_right

One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction–heterocyclization of 2-nitroacylbenzenes under neutral conditions

Jay chauhan

Tetrahedron Letters, 2012

View PDFchevron_right

A simple nitration of electrophilic alkenes with tetranitromethane in the presence of triethylamine. Synthesis of functionalized β-nitroalkenes

Yulia Volkova

Tetrahedron Letters, 2011

A convenient method for the preparation of functionalized b-nitroalkenes based on the nitration of a,adi-and a,a,b-trisubstituted unsaturated aldehydes, ketones and esters with tetranitromethane in the presence of triethylamine is described. Series of substituted b-nitroalcohols and b-nitroalkenes are obtained in good yields under mild conditions. Ó 2011 Elsevier Ltd. All rights reserved.

View PDFchevron_right

Indium mediated reductive heterocyclization of 2-nitroacylbenzenes or 2-nitroiminobenzenes toward 2,1-benzisoxazoles in aqueous media

youngoo Jin

Tetrahedron Letters, 2000

2-Nitro-substituted acylbenzenes or iminobenzenes such as 2-nitrobenzaldehydes, 2 -nitroacetophenone, and N-(2-nitrobenzylidene)anilines were cyclized toward 2,1-benzisoxazoles in the presence of 2-bromo-2-nitropropane and indium in an MeOH/H 2 O solution in excellent yields.

View PDFchevron_right

Loading...

Loading Preview

Sorry, preview is currently unavailable. You can download the paper by clicking the button above.

Ruthenium-Catalyzed Cycloaddition of Nitrile Oxides and Alkynes: Practical Synthesis of Isoxazoles

Valery Fokin

Angewandte Chemie International Edition, 2008

View PDFchevron_right

An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

pallavi sharma

Chemical Communications, 2010

View PDFchevron_right

A theoretical study of the mechanism and selectivity of the intramolecular 1,3-dipolar cycloaddition reaction of the nitrone– alkene derived from 2-allylthiobenzaldehyde for the synthesis of tricyclic isoxazolidines

Naim Kal

View PDFchevron_right

Synthesis of 1-Substituted Benzo [c] isoxazol-3 (1 H)-imines via Tandem Nitroso-Ene/Intramolecular Cyclizations of 2-Nitrosobenzonitrile

Jenna Jeffrey

The Journal of Organic …, 2008

View PDFchevron_right

Synthesis of isoxazolobenzoxepanes via Michael addition of indoles to nitroalkenes and sequential intramolecular nitrile oxide cycloaddition

D. Muralidharan, Paramasivan Perumal

Tetrahedron Letters, 2010

View PDFchevron_right

Nitroimidazoles, Part 1. An Unexpected Reactivity During the Cyclization of 3‐(4‐Amino‐1‐benzyl‐2‐ethyl‐1 H ‐imidazol‐5‐ylsulphanyl)‐propionic Acid Methyl Ester

Najim Al-Masoudi

Synthetic Communications, 2005

View PDFchevron_right

Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides

Patrick Rollin

Tetrahedron: Asymmetry, 2002

View PDFchevron_right

Intramolecular low-temperature 1,3-dipolar cycloadditions of nitrones: synthesis of chromano-heterocycles

Surinderjit S. Bhella

Tetrahedron, 2007

View PDFchevron_right

Organocatalysis ?on water?. Regioselective [3 + 2]-cycloaddition of nitrones and allenolates

Fernando garcia tellado

Chemical Communications, 2006

View PDFchevron_right

Enhanced rate of intramolecular nitrile oxide cycloaddition and rapid synthesis of isoxazoles and isoxazolines

Brindaban Roy

Monatshefte für Chemie - Chemical Monthly, 2010

View PDFchevron_right

Novel Formation of Aromatic Nitriles by Friedel-Crafts Reaction in Nitromethane

Masaaki Yoshifuji

Chemistry Letters, 1974

View PDFchevron_right

Electrochemical Synthesis of Heterocyclic Compounds; VII1. Anodic Synthesis of 1,3-Thiazole Derivatives

Ibro Tabakovic

Synthesis, 1979

View PDFchevron_right

Recent progress in the field of cycloaddition reactions involving conjugated nitroalkenes

Karolina Kula

Current Chemistry Letters, 2019

View PDFchevron_right

Electrophilically Activated Nitroalkanes in Double Annulation of [1,2,4]Triazolo[4,3-a]quinolines and 1,3,4-Oxadiazole Rings

Никита Кирилов

Molecules

View PDFchevron_right

Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles

Vy Duong

European Journal of Organic Chemistry, 2014

View PDFchevron_right

Regioselectivity associated with the 1,3-dipolar cycloaddition of nitrones with electron-deficient dipolarophiles

Augusto Rodriguez

Journal of Organic Chemistry, 1984

View PDFchevron_right

Multicomponent Macrocyclization Reactions (MCMRs) Employing Highly Reactive Acyl Ketene and Nitrile Oxide Intermediates

Mark Kurth

Organic Letters, 2011

View PDFchevron_right

The regioselectivity of nitrone and nitrile oxide cycloadditions to alkylidenecyclopropanes

Franca Cordero

Tetrahedron, 1992

View PDFchevron_right

A new facet of the reaction of nitro heteroaromatic compounds with ethyl isocyanoacetate

Takuji Ogawa

Journal of the Chemical Society, Perkin Transactions 1, 1996

View PDFchevron_right

1,3-Dipolar Cycloaddition Reactions and Nitrones : An Overview

Editor CSRL

View PDFchevron_right

The tandem cycloaddition chemistry of nitroalkenes

Atli Thorarensen

Pure and Applied Chemistry, 2000

View PDFchevron_right

Nitrone Cycloadditions to 1,2-Diphenylcyclopropenes and Subsequent Transformations of the Isoxazolidine Cycloadducts

Rafael Kostikov

Journal of Organic Chemistry, 2008

View PDFchevron_right

Tandem 6π-Electrocyclization and Cycloaddition of Nitrodienes to Yield Multicyclic Nitroso Acetals

Ohyun Kwon

Journal of the American Chemical Society, 2010

View PDFchevron_right

Nitrile Oxide 1,3-Dipolar Cycloaddition by Dehydration of Nitromethane Derivatives Under Continuous Flow Conditions

Paul Savage

Australian Journal of Chemistry, 2011

View PDFchevron_right

Synthesis of 3,4,5-Trisubstituted Isoxazoles in Water via a [3+2]-Cycloaddition of Nitrile Oxides and 1,3-Diketones, β-Ketoesters, or β-Ketoamides: Base-mediated and Keto-enol-controlled Mechanism

Imdadul Khan

2021

View PDFchevron_right

ChemistryOrganic ChemistryX Ray Crystallography