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Book Details
Abstract
It is well-established that organic synthetic processes have been at the core of the chemical industry for hundreds of years, in the production of organic compounds with a wide range of applications. However, we are becoming increasingly aware of the hazardous substances used and generated by these chemical processes. The field of organic synthesis has undergone profound changes to switch to equally efficient, but more sustainable processes that avoid the extensive use of toxic and hazardous reagents and solvents, harsh reaction conditions and expensive and sophisticated catalysts.
Explaining methods for carrying out chemical syntheses without the use of catalysts, this book shows how avoiding catalysts during synthesis can mean less use of toxic chemicals, environmentally damaging chemicals or endangered elements and lower costs. It is an important reference for chemists involved in organic synthesis, as well as for green chemists.
This book provides a broad overview over state-of-the-art catalyst-free reactions in organic synthesis. It is strongly recommended to chemical researchers as well as interested teachers and students.
Can Jin; College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P.R. China.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Contents | xi | ||
| Chapter 1 Catalyst-free Organic Synthesis: An Introduction | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 Catalyst-free Organic Synthesis – A Step Forward | 2 | ||
| 1.3 Overview of the Book | 3 | ||
| 1.4 How to Read | 3 | ||
| 1.5 Concluding Remarks | 4 | ||
| References | 4 | ||
| Chapter 2 Catalyst-free Organic Reactions under Room Temperature Conditions | 11 | ||
| 2.1 Introduction | 11 | ||
| 2.2 Room Temperature Organic Transformations Under Catalyst-free Conditions | 12 | ||
| 2.2.1 Entry-1: Synthesis of α-Amino Nitriles | 12 | ||
| 2.2.2 Entry-2: Synthesis of Tetraketones | 14 | ||
| 2.2.3 Entry-3: Synthesis of N-Heteroaryl α-Naphthylglycines | 18 | ||
| 2.2.4 Entry-4: Synthesis of bis(Hydroxyethyl)thioethers | 20 | ||
| 2.2.5 Entry-5: Synthesis of β-Hydroxy Thioesters | 21 | ||
| 2.2.6 Entry-6: Synthesis of Thioesters | 23 | ||
| 2.2.7 Entry-7: Synthesis of β-Sulfido Carbonyl Compounds | 25 | ||
| 2.2.8 Entry-8: Synthesis of S-alkyl Dithiocarbamates | 28 | ||
| 2.2.9 Entry-9: Synthesis of Densely Substituted Dithiocarbamates | 30 | ||
| 2.2.10 Entry-10: Synthesis of Pivalate Derivatives | 32 | ||
| 2.2.11 Entry-11: Synthesis of 2,20-Arylmethylenebis(3-Hydroxy-5,5-dimethyl-2-cyclohexene-1-one) Derivatives | 34 | ||
| 2.2.12 Entry-12: Synthesis of Aryl/Alkyl/Heteroarylsubstitutedbis(6-Amino-1,3-dimethyluracil-5-yl)methanes | 36 | ||
| 2.2.13 Entry-13: Synthesis of α-(Acyloxy)-α-(quinolin-4-yl)acetamides | 39 | ||
| 2.2.14 Entry-14: Synthesis of Endothiopeptides | 42 | ||
| 2.2.15 Entry-15: Synthesis of N-(Z-Alkenyl)imidazole-2-carbothioamides | 44 | ||
| 2.2.16 Entry-16: Synthesis of Spirooxindolepyrazolines | 47 | ||
| 2.2.17 Entry-17: Synthesis of γ-Aminoethers | 50 | ||
| 2.2.18 Entry-18: Synthesis of 1-Substituted-1Hpyrazoles | 52 | ||
| 2.2.19 Entry-19: Synthesis of 2-Thioparabanic Acids | 54 | ||
| 2.2.20 Entry-20: Synthesis of 5-amino-1,3-aryl-1Hpyrazole-4-carbonitriles | 56 | ||
| 2.2.21 Entry-21: Synthesis of Functionalized Azole Derivatives | 58 | ||
| 2.2.22 Entry-22: Synthesis of 1,2,4-Triazole Derivatives | 60 | ||
| 2.2.23 Entry-23: Synthesis of Amidated Fentanyl Analogs | 63 | ||
| 2.2.24 Entry-24: Synthesis of 3-(2-Pyrazolin-5-one) substituted-3-hydroxy-2-oxindoles | 65 | ||
| 2.2.25 Entry-25: Synthesis of 4,5-Disubstituted 2-Benzazepines | 68 | ||
| 2.2.26 Entry-26: Synthesis of Anthranilamide Schi. Bases | 71 | ||
| 2.2.27 Entry-27: Synthesis of 1,6-Dihydropyrazine-2,3-dicarbonitriles | 73 | ||
| 2.2.28 Entry-28: Synthesis of Polyhydroquinolines | 76 | ||
| 2.2.29 Entry-29: Synthesis of Functionalized 1,3,5-Trisubstituted Hydantoins | 79 | ||
| 2.2.30 Entry-30: Synthesis of 1,3,5-Trisubstituted-2-thiohydantoins | 82 | ||
| 2.2.31 Entry-31: Synthesis of 1,5-Disubstituted 1H-Tetrazoles | 86 | ||
| 2.2.32 Entry-32: Synthesis of 2-Thioxotetrahydropyrimidines | 88 | ||
| 2.2.33 Entry-33: Synthesis of Polycyclic Spiroindolines | 90 | ||
| 2.2.34 Entry-34: Synthesis of Fused Polyhalogeno-7α-hydroxy-[1,2-α]indol-5-one Derivatives | 92 | ||
| 2.2.35 Entry-35: Synthesis of Dialkyl-1,5-dihydro-5-oxo-1-phenyl-2H-[1]benzopyrano[ 2,3-b]pyridine-2,3-dicarboxylates | 95 | ||
| 2.2.36 Entry-36: Synthesis of 2-Aryl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-1,5-benzodiazepin-3-yl)acetamides | 97 | ||
| 2.2.37 Entry-37: Synthesis of Functionalized Tetrahydro-4-oxoindeno[1,2-b]pyrroles | 100 | ||
| 2.2.38 Entry-38: Synthesis of 4-(alkylamino)-1-(arylsulfonyl)-3-benzoyl-1,5-dihydro-5-hydroxy-5-phenyl-2H-pyrrol-2-ones | 102 | ||
| 2.2.39 Entry-39: Synthesis of 1,2-Dihydroisoquinoline Derivatives | 105 | ||
| 2.2.40 Entry-40: Synthesis of Arylsulfonamidosubstituted 1,5-Benzodiazepines | 107 | ||
| 2.2.41 Entry-41: Synthesis of N-(1,7-Dioxotetrahydropyrazolo[1,2-α]pyrazol-2-yl)-Benzamides | 108 | ||
| 2.2.42 Entry-42: Synthesis of Substituted Pyridin-2(1H)-ones | 110 | ||
| 2.2.43 Entry-43: Synthesis of Functionalized Pyrazolo[ 1,2-α][1,2,4]triazoles | 113 | ||
| 2.2.44 Entry-44: Synthesis of bis(Indolyl)-1,4-quinones | 115 | ||
| 2.2.45 Entry-45: Synthesis of Substituted 3-Hydroxy-2-oxindoles | 117 | ||
| 2.2.46 Entry-46: Synthesis of Pyrano[3,2-c]pyridines | 120 | ||
| 2.2.47 Entry-47: Synthesis of Iminofuranones | 122 | ||
| 2.2.48 Entry-48: Synthesis of Functionalized 5-Pyridylfuran-2-amines | 124 | ||
| 2.2.49 Entry-49: Synthesis of Functionalized γ-Iminolactones | 126 | ||
| 2.2.50 Entry-50: Synthesis ofFunctionalized bis(4H-Chromene) and 4H-Benzo[g]chromene derivatives | 130 | ||
| 2.2.51 Entry-51: Synthesis of SubstitutedCyclohepta[ b]pyran-3,4-dicarboxylate Derivatives | 135 | ||
| 2.2.52 Entry-52: Synthesis of 2-(Alkylimino)-7-oxo-1-oxa-6-azaspiro[4.4]nona-3,8-diene-3,4-dicarboxylates | 138 | ||
| 2.2.53 Entry-53: Synthesis of 2-Hydrazinylidene-3-hydroxy-4H-furo[3,2-c]pyran-4-ones | 141 | ||
| 2.2.54 Entry-54: Synthesis of Polyfunctionalized Iminospiro-γ-lactones | 143 | ||
| 2.2.55 Entry-55: Synthesis of Functionalized 2H-Indeno[2,1-b]furans | 145 | ||
| 2.2.56 Entry-56: Synthesis of 1,4-Benzoxazinones | 147 | ||
| 2.2.57 Entry-57: Synthesis of 1,3,4-Oxadiazoles | 149 | ||
| 2.2.58 Entry-58: Synthesis of 1,3-Thiazole-4(3H)-carboxylates | 152 | ||
| 2.2.59 Entry-59: Synthesis of Substituted 2-Aminothiazoles | 154 | ||
| 2.2.60 Entry-60: Synthesis of5-Hydrazinoethylidene-2-iminothiazolidinones | 156 | ||
| 2.2.61 Entry-61: Synthesis of Functionalized 2-Aminothiophenes | 159 | ||
| 2.2.62 Entry-62: Synthesis of 1,3,4-Selenadiazines | 162 | ||
| 2.2.63 Entry-63: Synthesis of Pyrazolyl 4H-Chromene Derivatives | 165 | ||
| 2.2.64 Entry-64: Synthesis of Oxazines | 169 | ||
| 2.2.65 Entry-65: Synthesis of N2-Alkyl-N3-[2-(1,3,4-oxadiazol-2-yl)aryl]benzofuran-2,3-diamines | 171 | ||
| 2.2.66 Entry-66: Synthesis of Functionalized 1,3,4-Oxadiazoles | 175 | ||
| 2.2.67 Entry-67: Synthesis of 2-(1,3,4-Oxadiazol-2-yl)-substituted 2-Hydroxy-1(2H)-acenaphthylenones | 178 | ||
| 2.2.68 Entry-68: Synthesis of Sterically-congested 1,3,4-Oxadiazoles | 180 | ||
| 2.2.69 Entry-69: Synthesis of 3-(5-Aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2-ones | 182 | ||
| 2.2.70 Entry-70: Synthesis of Hydrazinosubstituted Chromeno[2,3-c]pyrroles | 185 | ||
| 2.2.71 Entry-71: Synthesis of Substituted 3,4-Dihydrocoumarins | 188 | ||
| 2.2.72 Entry-72: Synthesis of bis(2-Arylimino-1,3-thiazolidin-4-one) Derivatives | 193 | ||
| 2.2.73 Entry-73: Synthesis of 2-(4-Oxo-1,3-thiazinan-5-yl)acetic acids | 195 | ||
| 2.2.74 Entry-74: Synthesis of Functionalized Pyrano[ 3,2-c]chromen-5(4H)-ones | 198 | ||
| 2.2.75 Entry-75: Synthesis of Functionalized Pyrano[ 3,2-c]chromen-5(4H)-ones | 203 | ||
| 2.3 Concluding Remarks | 208 | ||
| References | 209 | ||
| Chapter 3 Catalyst-free Organic Reactions with Conventional Heating | 219 | ||
| 3.1 Introduction | 219 | ||
| 3.2 Organic Transformations with Conventional Heating | 219 | ||
| 3.2.1 Entry-1: Synthesis of 1,2,4-Oxadiazoles | 219 | ||
| 3.2.2 Entry-2: Synthesis of Functionalized 5-Arylfuro[2,3-d]pyrimidin-4-ols | 221 | ||
| 3.2.3 Entry-3: Synthesis of 2-Methyl-4-amino-1,2,3,4-tetrahydroquinolines | 223 | ||
| 3.2.4 Entry-4: Synthesis of 2,3,7,12-Tetrahydrocyclopenta[ 5,6]pyrido[2,3-c]carbazol-1(4H)-ones and3,4,7,12-Tetrahydro-1Hfuro[ 30,40:5,6]pyrido[2,3-c]carbazol-1-ones | 227 | ||
| 3.2.5 Entry-5: Synthesis of Substituted Pyrimidine Derivatives | 229 | ||
| 3.2.6 Entry-6: Synthesis of 2-Aryl-5-cyano-4-methylsulfanylpyrimidin-6-ones | 232 | ||
| 3.2.7 Entry-7: Synthesis of Phosphonated 2(1H)-Pyrazinones | 235 | ||
| 3.2.8 Entry-8: Synthesis of Nitrogen-containing Bicyclic Derivatives | 237 | ||
| 3.2.9 Entry-9: Synthesis of Trifluoromethylsubstituted Bicyclic Pyridines | 239 | ||
| 3.2.10 Entry-10: Synthesis of Spiro[indoline-3,20-pyrroles] | 243 | ||
| 3.2.11 Entry-11: Synthesis of 4-(2-Substituted-3-iminoisoindolin-1-ylidene)-1-substituted-3-methyl-1H-pyrazol-5(4H)-ones | 245 | ||
| 3.2.12 Entry-12: Synthesis of β-Lactam-triflones | 247 | ||
| 3.3 Concluding Remarks | 250 | ||
| References | 250 | ||
| Chapter 4 Catalyst-free Reactions with Microwave Irradiation | 253 | ||
| 4.1 Introduction | 253 | ||
| 4.2 Catalyst-free Organic Transformations with Microwave Irradiation | 253 | ||
| 4.2.1 Entry-1: Synthesis of C-Alkylated Indoles | 254 | ||
| 4.2.2 Entry-2: Synthesis of Sulfonamides | 255 | ||
| 4.2.3 Entry-3: Synthesis of 4-Hydroxy-3-arylthiazolidine-2-thiones | 257 | ||
| 4.2.4 Entry-4: Synthesis of 1,4-Dihydro-5-hydroxy-2-methyl-N,4-diphenylquinoline-3-carboxamides | 259 | ||
| 4.2.5 Entry-5: Synthesis of Azaarene-substituted 3-hydroxy-2-oxindoles | 262 | ||
| 4.2.6 Entry-6: Synthesis of Functionalized Quinoline Derivatives | 265 | ||
| 4.2.7 Entry-7: Synthesis of Quinoxalines | 267 | ||
| 4.2.8 Entry-8: Synthesis of Coumarin-substituted Quinoxalines | 269 | ||
| 4.2.9 Entry-9: Synthesis of Functionalized 1,8-Naphthyridines and Quinolines | 271 | ||
| 4.2.10 Entry-10: Synthesis of Substituted Pyrazoles | 273 | ||
| 4.2.11 Entry-11: Synthesis of Substituted Tetrahydropyrimidines | 274 | ||
| 4.2.12 Entry-12: Synthesis of 1-Carboxymethyl-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles | 278 | ||
| 4.2.13 Entry-13: Synthesis of 5,6-Dihydropyrido[4,3-d]pyrimidines and Pyrido[4,3-d]pyrimidines | 280 | ||
| 4.2.14 Entry-14: Synthesis of 2,4,5-Triarylimidazoles | 284 | ||
| 4.2.15 Entry-15: Synthesis of 7-Amino-substituted Pyrazolo[ 1,5-α][1,3,5]triazine-8-carbonitriles | 286 | ||
| 4.2.16 Entry-16: Synthesis of Spiroindenotetrahydropyridines | 289 | ||
| 4.2.17 Entry-17: Synthesis ofOxazolo[5,4-b]quinoline-fused Spirooxindoles | 293 | ||
| 4.2.18 Entry-18: Synthesis of Substituted Fused Pyrans | 295 | ||
| 4.2.19 Entry-19: Synthesis of Ring-fused Aminals | 298 | ||
| 4.2.20 Entry-20: Synthesis of Substituted6H-Benzo[c]chromenes and 6H-Benzo[c]-chromen-8-ols | 301 | ||
| 4.2.21 Entry-21: Synthesis of Functionalized 1,4-Pyranonaphthoquinones | 303 | ||
| 4.2.22 Entry-22: Synthesis of α-Aminophosphonates | 306 | ||
| 4.3 Concluding Remarks | 308 | ||
| References | 308 | ||
| Chapter 5 Catalyst-free Organic Reactions with Ultrasound Irradiation | 314 | ||
| 5.1 Introduction | 314 | ||
| 5.2 Catalyst-free Organic Transformations with Ultrasound Irradiation | 315 | ||
| 5.2.1 Entry-1: Synthesis of N-formylated Derivatives | 315 | ||
| 5.2.2 Entry-2: Synthesis of Silyl Ethers | 316 | ||
| 5.2.3 Entry-3: Synthesis of Substituted Thiourea Derivatives | 318 | ||
| 5.2.4 Entry-4: Synthesis of α-Aminophosphonates | 321 | ||
| 5.2.5 Entry-5: Synthesis of 4,40-(Arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) s | 323 | ||
| 5.2.6 Entry-6: Synthesis of Substituted Dihydroquinolines | 327 | ||
| 5.2.7 Entry-7: Synthesis of Substituted 1,4-Dihydropyridines | 329 | ||
| 5.2.8 Entry-8: Synthesis of Substituted Quinoxalines | 332 | ||
| 5.2.9 Entry-9: Synthesis of Substituted Dispiropyrrolizidines | 335 | ||
| 5.2.10 Entry-10: Synthesis of 7-Methyl-substituted Pyrido[4,3-d]pyrimidine Derivatives | 338 | ||
| 5.2.11 Entry-11: Synthesis of 6H-1-Benzopyrano[4,3-b]quinolin-6-ones | 341 | ||
| 5.2.12 Entry-12: Synthesis of Rhodanines | 343 | ||
| 5.2.13 Entry-13: Synthesis of Formamidines | 346 | ||
| 5.2.14 Entry-14: Synthesis of Thiazolo[3,2-α]pyrimidines | 348 | ||
| 5.2.15 Entry-15: Synthesis of Thiazolo[3,2-α]pyrimidines | 350 | ||
| 5.2.16 Entry-16: Synthesis of Spiro[indoline-3,40-pyrazolo[3,4-e][1,4]thiazepine]diones | 353 | ||
| 5.3 Concluding Remarks | 356 | ||
| References | 356 | ||
| Chapter 6 Catalyst-free Organic Reactions with Ball Milling | 365 | ||
| 6.1 Introduction | 365 | ||
| 6.2 Catalyst-free Organic Transformations with Ball Milling | 366 | ||
| 6.2.1 Entry-1: Synthesis of Pyrroles | 366 | ||
| 6.2.2 Entry-2: Synthesis of Substituted Benzimidazolidine-2-thiones | 368 | ||
| 6.2.3 Entry-3: Synthesis of Quinoxaline Derivatives | 369 | ||
| 6.2.4 Entry-4: Synthesis of 2-Oxo/thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles | 372 | ||
| 6.2.5 Entry-5: Synthesis of Phenyl Boronate Esters | 374 | ||
| 6.2.6 Entry-6: Synthesis of Boronic Acid Esters | 376 | ||
| 6.3 Concluding Remarks | 377 | ||
| References | 378 | ||
| Subject Index | 381 |