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Targets in Heterocyclic Systems TARGETS IN HETEROCYCLIC SYSTEMS Chemistry and Properties Volume 7 (2003) Reviews and Accounts on Heterocyclic Chemistry http://www.sci.uniba.it Editors Prof. Orazio A. Attanasi Institute of Organic Chemistry, University of Urbino Urbino, Italy and Prof. Domenico Spinelli Department of Organic Chemistry, University of Bologna Bologna, Italy Italian Society of Chemistry Division of Organic Chemistry Division of Medicinal Chemistry Division of Mass Spectrometry Published by: Società Chimica Italiana Viale Liegi, 48 00198 Roma Italy ___________________________________________________________________________ Copyright © 2003 Società Chimica Italiana All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means (electronic, electrostatic, magnetic tape, mechanical, photocopying, recording or otherwise) without permission in writing from the publishers. A person may photocopy an article for personal use. Volume 1 (1997) First edition 1997 ISBN 88-86208-24-3 Second edition 1999 ISBN 88-86208-24-3 Volume 2 (1998) First edition 1999 ISBN 88-86208-11-1 Volume 3 (1999) First edition 2000 ISBN 88-86208-13-8 Volume 4 (2000) First edition 2001 ISBN 88-86208-16-2 Volume 5 (2001) First edition 2002 ISBN 88-86208-19-7 Volume 6 (2002) First edition 2003 ISBN 88-86208-23-5 Volume 7 (2003) First edition 2004 ISBN 88-86208-28-6 ISSN 1724-9449 Printed and bound in Italy by: Arti Grafiche Editoriali s.r.l. Via S. Donato, 148/C 61029 Urbino (Pesaro-Urbino) Italy April 2004 Editorial Advisory Board Members Prof. Enrico Aiello Prof. Lucedio Greci University of Palermo University of Ancona Palermo, Italy Ancona, Italy Prof. Jan Bergman Prof. Laurence M. Harwood Karolinska Institute University of Reading Huddinge, Sweden Reading, UK Prof. José A. S. Cavaleiro Prof. Victor G. Kartsev University of Aveiro University of Moscow Aveiro, Portugal Moscow, Russia Prof. Leopoldo Ceraulo Prof. Steven V. Ley University of Palermo University of Cambridge Palermo, Italy Cambridge, England Prof. Carlo Dell'Erba Prof. Alexander McKillop University of Genova University of East Anglia Genova, Italy Norwich, England Dr. Daniele Donati Prof. Giovanni Sindona Glaxo Wellcome University of Calabria Verona, Italy Arcavacata di Rende, Italy Prof. José Elguero Prof. Branko Stanovnik CSIC University of Ljubljana Madrid, Spain Ljubljana, Slovenia Prof. Hussein El-Kashef Prof. Richard J. K. Taylor University of Assiut University of York Assiut, Egypt York, England Prof. Dieter Enders Prof. Eric J. Thomas RWTH University of Manchester Aachen, Germany Manchester, England Prof. Leon Ghosez Dr. Mario Varasi Catholic University of Louvain Pharmacia & Upjohn Louvain la Neuve, Belgium Nerviano, Italy Dr. Gianluca Giorgi Prof. Kirill N. Zelenin University of Siena Military Medical Academy Siena, Italy St. Petersburg, Russia Indexed/Abstracted in: Chemical Abstracts; Current Contents; ISI/ISTP&B online database; Index to Scientific Book Contents; Chemistry Citation Index; Current Book Contents; Physical, Chemical & Earth Sciences; Methods in Organic Synthesis; The Journal of Organic Chemistry; La Chimica e l'Industria; Synthesis. Dear Reader, Volume 7 (2003) keeps the international standard of THS series and contains eleven chapters, covering the synthesis, reactivity, and mass spectrometry of different heterorings. Reviews from Italy, Russia, and Spain are present in this book. Comprehensive Reviews reporting the overall state of the art on wide fields as well as personal Accounts highlighting significative advances by research groups dealing with their specific themes have been solicited from leading Authors. The submission of articles having the above-mentioned aims and concerning highly specialistic topics is strongly urged. The publication of Chapters in THS is free of charge. Firstly a brief layout of the contribution proposed, and then the subsequent manuscript, may be forwarded either to a Member of the Editorial Board or to one of the Editors. The Authors, who contributed most competently to the realization of this Volume, and the Referees, who cooperated unselfishly (often with great patience) spending valuable attention and time in the review of the manuscripts, are gratefully acknowledged. Orazio A. Attanasi and Domenico Spinelli Editors Table of Contents (for the contents of Volumes 1-6 please visit: http://www.sci.uniba.it) Regio- and stereoselective addition reactions of carbon nucleophiles to epoxides 1 Paolo Crotti, Valeria Di Bussolo, Franco Macchia and Mauro Pineschi 1. Introduction 2. Enantioselective addition of dialkylzinc reagents to allylic epoxides. 2.1. Copper-catalyzed kinetic resolution of allylic epoxides with dialkylzinc reagents. 2.2. Copper-catalyzed enantioselective desymmetrization of symmetrical allylic epoxides. 2.3. Copper-catalyzed enantioselective desymmetrization of symmetrical allylic 1,4- epoxides. 2.4. Regiodivergent kinetic resolution of allylic epoxides. 3. Addition reaction of lithium enolates of simple ketones to 1,2-epoxides. A new reaction 3.1. Li+- and Y+3-promoted addition of lithium enolates of ketones to epoxides. Synthesis of γ−hydroxy ketones. 3.2. Sc+3-promoted addition of lithium enolates of ketones to epoxides. Diastereoselectivity of the reaction. 3.3. Intramolecular version of the addition reaction. Cyclization of epoxy ketones. 3.4. Synthesis of enantiomerically pure γ-hydroxy ketones. 3.5. Enantioselective addition of lithium enolate of acetophenone to cycloalkene oxides. 3.6. A recent new protocol for the addition of lithium enolate of ketones to 1,2- epoxides. 4. Conclusions Acknowledgements References and Notes Recent developments in the chemistry of isoxazol-5-ones 31 Egle Maria Beccalli, Donato Pocar and Caterina Zoni 1. Introduction 2. Properties of isoxazol-5-ones 3. Preparation of isoxazol-5-ones 3.1. Synthetic approaches to substituted isoxazol-5-ones 3.2. Isoxazol-5-ones by intramolecular cyclization 3.3. Synthetic approaches to 4-alkylideneisoxazol-5-ones 4. Reactions of isoxazol-5-ones 4.1. N-, O- and C-alkylation and acylation of isoxazol-5-ones 4.2. Halogenation reactions of isoxazol-5-ones 4.3. Reaction of isoxazol-5-ones with electrophilic reagents 4.4. Vilsmeier-Haack reaction of isoxazol-5-ones I 4.5. 4-Nitroisoxazol-5-ones 4.6. Thermolysis and photolysis of isoxazol-5-ones 4.7. Michael additions of ylides to arylmethyleneisoxazol-5-ones 4.8. Reduction of arylmethyleneisoxazol-5-ones 4.9. Alkynes from isoxazol-5-ones 4.10. Cycloaddition reactions 5. Heterocycles from isoxazol-5-ones 6. Pharmaceutical studies on isoxazol–5-ones References Application of microwave irradiation, solid supports and catalysts in environmentally 64 benign heterocyclic chemistry José Ramón Carrillo, Ángel Díaz-Ortiz, Antonio de la Hoz, Andrés Moreno, María Victoria Gómez, Pilar Prieto, Ana Sánchez-Migallón and Ester Vázquez 1. Introduction 2. Microwave activation in environmentally friendly heterocyclic chemistry 2.1. Synthesis of coumarin derivatives 2.1.1. Synthesis of dihydrocoumarin and coumarin derivatives. Modification of the Pechmann reaction 2.1.2. Pechmann reaction 2.2. Tandem Diels–Alder aromatization reaction of furans 2.2.1. Diels–Alder reaction of furans 2.2.2. Synthesis of benzene derivatives by ring-opening of Diels–Alder cycloadducts 2.3. Preparation of <- and =-substituted alanine derivatives 2.4. Synthesis of 1,3,5-triazines 2.5. Synthesis of quinoxaline-2,3-dione: a synthetic model for radiolabeled compounds 3. Conclusions Acknowledgements References Intramolecular palladium-catalysed annulations: advances in azapolycyclic 86 indole synthesis Elisabetta Rossi and Giorgio Abbiati 1. Introduction 2. a-Azaannulated polycyclic indoles by intramolecular palladium-catalysed C-N bond formation 3. b-Azaannulated polycyclic indoles by intramolecular palladium-catalysed C-C bond formation II 4. b-Azaannulated polycyclic indoles by intramolecular palladium-catalysed C-N bond formation References Hetero diels-alder approach to oxathiins 108 Stefano Menichetti and Cristina Nativi 1. Introduction 2. Synthesis of oxathiins by classical methods 2.1. Oxathiins from acyclic precursors 2.2. Oxathiins from cyclic precursors 2.3. Synthesis of benzoxathiins 3. Diels-Alder approach to oxathiins 3.1. Early results 3.2. ,’-Dioxothiones as electron-poor dienes 3.3. ortho-Thioquinones as electron-poor dienes 3.4. Glycals as dienophiles 4. Reactivity of 1,4-oxathiins 4.1. Ring opening 4.2. Oxidation and reduction 4.3. Glyco-condensed oxathiins 5. Applications of 1,4-oxathiins 6. Conclusions Acknowledgements References Nucleophilic additions to nitrones: an alternative gateway to isoxazolidines, 140 pyrrolidines and related compounds Pedro Merino 1. Introduction 2. Synthesis of isoxazolidines and related compounds 3. Synthesis of pyrrolidines and related compounds 4. Conclusions Acknowledgements References Paternó-Büchi reaction on furan: regio- and stereochemistry 157 Maurizio D’Auria 1. Introduction 2. The Paternò-Büchi reaction on furan derivatives 3. Approaches to the explanation of regio- and stereoselectivity 3.1. Greisbeck rule III 3.2. Scharf rule 4. Asymmetric reactions 5. An explantion of diastereoselectivity 6. Reactions in zeolites 7. Diastereoselectivity in the reaction with furylmethanol derivatives (Adam rule) References Mass spectrometry of simple indoles part 1: electron ionisation, photo-ionisation 174 and electron capture ionisation David Bongiorno, Lorenzo Camarda, Leopoldo Ceraulo and Mirella Ferrugia 1. Introduction 2. Electron ionisation 2.1.
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