Saturated Heterocyclic Chemistry (v. 3) PDF
Preview Saturated Heterocyclic Chemistry (v. 3)
A Specialist Periodical Report Saturated Heterocyclic Chemistry Volume 3 A Review of the Literature Published during 1973 Sen io r Reporter M. F. Ansell, Queen Mary College, London Reporters D. J. Maitland, University of Bradford J. M. Mellor, University of Southampton A. E. A. Porter, University of Stirling B. Walker, Queen’s University, Belfast 0 Copyright I975 The Chemical Society Burlington House, London, W IV OBN. ISBN: 0 85186 562 3 Library of Congress Catalog Card No. 72-83454 Printed in Northern Ireland at The Universities Press, Belfast Fore word The third volume of this Specialist Periodical Report reviews developments in the field of Saturated Heterocyclic Chemistry for the period January- December 1973. The format of the Report follows that of Volume 2, except for the omission of the chapter on Medium-sized Rings. It is intended to remedy this unfortunate omission by including a two-year Report (1973 and 1974) in Volume 4. The production of this volume is due to the skill and patience with which the contributors have compiled their Reports and the expert assistance of the Chemical Society Editorial Staff. I express to all of them my sincere thanks. April 1975 M. F. Ansell Cont ents Chapter I Three-membered Rings 1 By D. /. Maitland 1 Introduction 1 2 Oxirans 1 Formation 1 Direct Insertion 1 Oxygen atom insertion 1 Carbon atom insertion 12 Cyclization of Halohydrin 16 Darzens Reaction 19 Met al-cata 1 y sed Epoxidati on 22 Miscellaneous 24 Reactions 28 Ring-opening 28 Electrophilic 28 Nucleophilic 32 Dipolar cycloaddition 40 Rearrangement 41 Ring Retention 45 Miscellaneous 46 3 Aziridines 49 Format ion 49 Direct Insertion of Nitrogen or Carbon Atoms 49 Cyclizati on 51 Ring Contraction 59 Formation via Azirines 60 React ions 62 Ring-o pening 62 Electrophilic and nucleophilic 62 Dipolar cycloaddition 65 Rearrangement 69 Ring Retention 70 4 Thiirans 73 Formation 73 Carbon Atom Insertion 73 Sulphur Atom Insertion 77 Cyclization 77 Miscellaneous 77 Episulphoxides 79 V vi Contents Reactions 80 Ring-opening 80 Desulphurization 81 Ring Expansion 82 5 Rings containing More than One Heteroatom 82 Formation 82 Diaziridines 82 Oxaziridines 84 Azaphosphiridines 84 Thiadiaziridine 1,l-Dioxides 85 React ions 85 Diaziridines 85 Oxaziridines 87 Thiadiaziridine 1,l-Dioxides 90 Chapter 2 Four-membered Rings 92 By B. 1. Walker 1 Introduction 92 2 Physical Methods 92 Magnetic Resonance 92 Miscellaneous 94 3 Formation 94 Oxetans 94 Cyclization 94 + [2 21 Cycloaddition 96 Miscellaneous 99 Azetidines 100 Cyclizati on 100 + 12 21 Cycloaddition 103 Ring Contraction 112 Miscellaneous 113 Rings containing More than One Heteroatom 117 Cyclization 117 + [2 21 Cycloaddition 118 Miscellaneous 121 4 Reactions 122 Oxetans 122 Ring-o pening 122 Rearrangement 125 Miscellaneous 126 Azet idines 127 Ring-opening 127 Rearrangement 128 Miscellaneous 131 Con tents vii Rings containing More than one Heteroatom 136 Ring-opening 136 Chapter 3 Five- and Six-membered Rings and Related Fused Systems 138 By A. E. A. Porter 1 Introduction 138 2 Conformational Analysis of Reduced Heterocycles 138 General 138 Oxygen-containing Rings 139 Nitrogen-containing Rings 144 Phosphorus-containing Rings 151 Sulphur-containing Rings 154 3 Cycloaddition Reactions 158 + [3 21 Cycloaddition 158 General 158 Ni trones 159 Nitrile Imines 161 Nitrile Oxides 161 Nitrile Ylides 163 Azides and Diazoalkanes 165 Miscellaneous 166 + [4 21 Cycloaddition 166 Oxygen-containing Rings 16 6 Nitrogen-containing Rings 168 Rings containing both Oxygen and Nitrogen 169 4 General Chemistry of Saturated Heterocycles 170 Oxygen containing Rings 170 Tetrahydrofurans 170 Dihy drofurans 172 Lactones 174 Miscellaneous Furanoid Derivatives 176 1, ZDioxolans 177 1,3-Dioxolans 177 Ozonides 179 Tet rahy dropy rans 180 Di hydropyrans 181 Dihydropyrones 183 Fused Pyrans 184 1, ZDioxans 184 lY3-Dioxans 185 1,4-Dioxans 185 Miscellaneous 185 viii Contents Nitrogen-containing Rings 186 Pyrrolidines 186 Pyrrolidones 189 Dihy dropy rroles 190 Pyrazolines 19 4 Imidazolines 197 Triazolines 200 Tetrazolines 202 Piperidines 202 Piperidones 204 Tetr ahy dropyridines 205 Dihy dropyridines 207 Quinoline Derivatives 208 Isoquinoline Derivatives 209 Aza-steroids 210 Fused Systems 21 1 Hexahy dropyridazines 212 Tetrahyd r opyridazines 212 Dihy dropyridazines 213 Cinnoline Derivatives 213 Phthalazine Derivatives 214 Pyrimidine Derivatives 214 Piperazines 216 Dihydropy razines 217 Piperazinediones 21 8 Fused Pyrazines 221 1,2,4-Triazines 222 1,3,5-Triazines 223 Condensed Triazines 223 Tet r azines 224 Fused Tetrazines 226 Rings containing both Oxygen and Nitrogen 226 Isoxazole Derivatives 226 Oxazole Derivatives 229 Fused Oxazoles 236 Dioxazoles 236 Oxadiazoles 237 1,2-Oxazines 238 1,3-0xazines 239 Fused 1,3-Oxazines 241 1,4-0xazines 242 Dioxazines 243 Oxadiazines 244 Miscellaneous Fused Systems 245
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