Synthesis of Heterocycles via Cycloadditions I / Edition 1

by Alfred Hassner

Overview

Heterocyclicmoleculesplayasigni?cantroleinlifeprocessesandhaveplayed a major rolein industrial developments of the last century, for instance in the ?eld of dyes, pharmaceuticals, pesticides, polymers etc. They comprise not onlysomeofthemostinterestingandbiologicallyimportantnaturalproducts like alkaloids, carbohydrates, nucleic acids, and antibiotics but include many practical drugs and a large segment of known synthetic organic compounds. Hencescientistshavedevotedagreatamountofeffortto?ndoptimalsynthetic approachesto a variety ofheterocyclic compounds. Amongthemostsuccessfulandselectivesyntheticprocessesarecycload- tionreactions,since theyinvolvesimultaneous orsequential formationoftwo ormorebondsoftenwithahighdegreeofstereoselectivityandregioselectivity. Forinstance, 1,3 dipolar cycloadditionsareelectronicallyequivalent to Diels- Alder reactions and are among the most common 5-membered ring-forming systems. In addition they usually proceed with a high degree of stereo- and regio-control.It is therefore, not surprising that synthesis of many important classesofheterocycles,includingthoseofusefulbiologicallyactivemolecules, haveutilized cycloadditionsteps intheir formation.Furthermore,manyhe- rocyclesserve as intermediates in the synthesis of polyfunctional molecules. In this volume we present ?ve selected contributions by well-known - thors, each an authority in his ?eld. The ?rst chapter deals with construction ofisoxazolines(dihydroisoxazoles)via1,3-dipolarcycloadditionsofnitronates or of nitrile oxides generated from nitroalkanes. This includes inter- as well as intramolecular processes. Many of these heterocycles possess important synthetic and biological properties and are shown to lead to stereo- and - gioselectiveintroductionofmultifunctionalmoleculessuchasaminoalcohols, ?-amino acids, aldols, nitriles, and others.

Product Details

ISBN-13:	9783540783688
Publisher:	Springer Berlin Heidelberg
Publication date:	08/27/2008
Series:	Topics in Heterocyclic Chemistry , #12
Edition description:	2008
Pages:	229
Product dimensions:	6.10(w) x 9.00(h) x 0.40(d)

Table of Contents

Isoxazolines from Nitro Compounds: Synthesis and Applications.- Cycloaddition Reactions of Azides Including Bioconjugation.- Enantioselective Cycloadditions of Azomethine Ylides.- Heterocycles by Cycloadditions of Carbonyl Ylides Generated from Diazo Ketones.- Heterocycles from Unsaturated Phosphorus Ylides.