Larina L. Nitroazoles: synthesis, structure and applications / L.Larina, V.Lopyrev. - Dordrecht; New York: Springer, 2009. - xviii, 441 p.: ill. - (Topics in applied chemistry). - Incl. bibl. ref. - Ind.: p.435-441. - ISBN 978-0-387-98069-0  Место хранения:   054 | Международный томографический центр CO РАН | Новосибирск

Оглавление / Contents

Introduction ................................................... xv Synthesis of Five-Membered Nitroazoles .......................... 1 Electrophilic Nitration of Azoles ............................... 1 Electrophilic Nitration Mechanism ............................ 2 Nitration with Nitric Acid or Sulfuric-Nitric Acid Mixture ... 5 Kinetics and Mechanism of Nitration of Azoles by Sulfuric-Nitric Acid Mixture ............................. 21 Nitration by Other Nitrating Agents ......................... 25 Iрsо-Nitration of Azoles .................................... 32 Synthesis from Aminoazoles ..................................... 35 Synthesis Based on Heterocyclization ........................... 40 Synthesis from Various Cyclic Systems .......................... 49 Other Methods of Preparation ................................... 55 Polynitroazoles ................................................ 60 Conclusions .................................................... 64 References ..................................................... 64 Synthesis of Nitrobenzazoles ................................... 81 Introduction ................................................... 81 Nitration of Benzazoles ........................................ 82 Indazoles ................................................... 82 Benzimidazoles ............................................. 84 Benzisoxazoles, Benzoxazoles, and Benzoxadiazoles ........... 87 Benzisothiazoles, Benzothiazoles, and Benzothiadiazoles ..... 91 Benzoselenazoles and Benzoselenodiazoles .................... 93 Benzotriazoles .............................................. 93 Synthesis of Nitrobenzazoles via Heterocyclization ............. 95 Nitroindazoles .............................................. 95 Nitrobenzimidazoles ........................................ 102 Nitrobenzisoxazoles, Nitrobenzoxazoles, and Nitrobenzoxadiazoles ....................................... 109 Nitrobenzisothiazoles, Nitrobenzothiazoles, and Nitrobenzothiadiazoles ................................. 120 Nitrobenzisoselenazoles, Nitrobenzoselenazoles, and Nitrobenzoselenodi azoles .............................. 130 Nitrobenzotriazoles ........................................ 130 Other Methods of Synthesis .................................... 136 The Sandmeyer Reaction ..................................... 136 Recyclization .............................................. 137 Conclusions ................................................... 140 References .................................................... 141 Structure and Physical-Chemical Properties of Nitroazoles ..... 157 Molecular and Crystalline Structure ........................... 157 Nuclear Magnetic Resonance .................................... 181 Pyrazoles .................................................. 182 Imidazoles.................................................. 199 Isoxazoles, Oxazoles, and Oxadiazoles ...................... 206 Isothiazoles, Thiazoles, and Thiadiazoles .................. 215 Triazoles and Tetrazoles ................................... 217 Indazoles .................................................. 229 Benzimidazoles ............................................. 236 Benzoxazoles, Benzisoxazoles, and Benzofurazans ............ 245 Benzothiazoles, Benzothiadiazoles, and Benzoselenazoles .... 253 Benzotriazoles ............................................. 256 Conclusions ................................................ 262 Electron Spin Resonance Spectroscopy .......................... 263 Polarography .................................................. 280 Infrared Spectroscopy ......................................... 295 Nitropyrazoles ............................................. 295 Nitroimidazoles ............................................ 297 Nitroisoxazoles, Nitrooxazoles, and Nitrooxadiazoles ....... 298 Nitroisothiazoles and Nitrothiazoles ....................... 300 Nitrotriazoles ............................................. 302 Nitrotetrazoles ............................................ 305 Nitroindazoles ............................................. 305 Nitrobenzimidazoles ........................................ 307 Nitrobenzisoxazoles, Nitrobenzoxazoles, and Nitrobenzoxadiazoles ....................................... 308 Nitrobenzoselenodiazoles ................................... 310 Nitrobenzothiazoles ........................................ 310 UV Spectroscopy ............................................... 310 Nitropyrazoles ............................................. 310 Nitroimidazoles ............................................ 313 Nitroisoxazoles, Nitrooxazoles, and Nitrooxadiazoles ....... 316 Nitroisothiazoles and Nitrothiazoles ....................... 317 Nitrotriazoles ............................................. 318 Nitrotetrazoles ............................................ 321 Nitroindazoles ............................................. 321 Nitrobenzimidazoles ........................................ 322 Nitrobenzoxazoles and Nitrobenzoxadiazoles ................. 324 Nitrobenzothiazoles and Nitrobenzothiadiazoles ............. 327 Nitrobenzotriazoles ........................................ 328 Dipole Moments ................................................ 328 Mass Spectrometry ............................................. 332 Nitropyrazoles ............................................. 332 Nitroimidazoles ............................................ 336 Nitroisoxazoles ............................................ 341 Nitroisothiazoles, Nitrothiazoles, and Nitrothiadiazoles ... 345 Nitrotriazoles and Nitrotetrazoles ......................... 346 Nitroindazoles ............................................. 350 Nitrobenzimidazoles ........................................ 352 Nitrobenzisoxazoles, Nitrobenzoxazoles, and Nitrobenzoxadiazoles ....................................... 357 Nitrobenzoisothiazoles, Nitrobenzothiazoles, and Nitrobenzothiadiazoles ................................. 360 Nitrobenzoselenodiazoles ................................... 360 Nitrobenzotriazoles ........................................ 363 Conclusions ................................................... 364 Other Physical-Chemical Properties ............................ 364 References .................................................... 373 Application of Nitroazoles .................................... 407 Introduction .................................................. 407 Five-Membered Nitroazoles ..................................... 408 Nitrobenzazoles ............................................... 423 Conclusions ................................................... 423 References .................................................... 424 Abbreviations ................................................. 433 Index ......................................................... 435