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Preface xvii 1 Synthesis of Diverse Nitrogen Heterocycles Explored in Denitrogenative Transformations 1 Monalisa Akter and Pazhamalai Anbarasan
1.1 Introduction 1
1.2 Synthesis of 1,2,3-Triazoles 1
1.2.1 Synthesis of NH-Triazoles 1
1.2.2 Synthesis of N-Sulfonyl-1,2,3-triazoles 6
1.2.3 Synthesis of N-Trifluoromethyl-1,2,3-triazoles 8
1.2.4 Synthesis of 5-Iodo-1,2,3-triazoles 10
1.2.5 Synthesis of Pyridotriazoles 11
1.2.6 Synthesis of Triazoloindoles 12
1.2.7 Synthesis of Benzotriazoles 12
1.3 Synthesis of 1,2,3-Thiadiazoles 13
1.4 Synthesis of Tetrazoles 13
1.4.1 Synthesis of 1H-Tetrazoles 13
1.4.2 Synthesis of Pyridotetrazoles 15
1.4.3 Synthesis of Tetrazolo[1,5-a]quinolines 16
1.5 Synthesis of 3-Aminoindazoles 17
1.6 Synthesis of Benzotriazinones 18
1.7 Summary and Outlook 20 References 20 2 Transannulation of N-Sulfonyl-1,2,3-triazoles with Polar Multiple Bonds 31 Chuan-Ying Li and Ze-Feng Xu
2.1 Introduction 31
2.2 Reaction of N-Sulfonyl-1,2,3-triazoles with Carbonyls 31
2.3 Reaction of N-Sulfonyl-1,2,3-triazoles with Nitriles 42
2.4 Reaction of N-Sulfonyl-1,2,3-triazoles with Polar Multiple Bonds Beyond Carbonyls and Nitriles 44
2.5 Conclusion 47 References 47 3 Transannulation of N-Sulfonyl-1,2,3-triazoles with Nonpolar Multiple Bonds such as Alkenes, Alkynes, and Allenes 51 Prasiddha Nagarajan, Akhil Rampally, and Sudam G. Dawande
3.1 Introduction 51
3.2 Transannulation of N-Sulfonyl-1,2,3-triazoles with Alkenes 52
3.2.1 Intermolecular Transannulation with Alkenes 52
3.2.2 Intramolecular Transannulation with Alkenes 63
3.3 Transannulation of N-Sulfonyl-1,2,3-triazoles with 1,3-Dienes 64
3.3.1 Intermolecular Transannulation with 1,3-Dienes 65
3.3.2 Intramolecular Transannulation with 1,3-Dienes 68
3.4 Transannulation of N-Sulfonyl-1,2,3-triazoles with Alkynes 69
3.4.1 Intermolecular Transannulation with Alkynes 69
3.4.2 Intramolecular Transannulation with Alkynes 73
3.5 Transannulation of N-Sulfonyl-1,2,3-triazoles with Allenes 75
3.5.1 Intermolecular Transannulation with Allenes 75
3.5.2 Intramolecular Transannulation with Allenes 78
3.6 Summary and Outlook 79 References 80 4 Transannulations of N-Sulfonyl-1,2,3-triazoles with Carbo/Heterocycles 83 Mikhail S. Novikov and Nikolai V. Rostovskii
4.1 Introduction 83
4.2 Transannulations with Ring Retention 85
4.2.1 Aromatic and Heteroaromatic Rings 85
4.2.2 Nonaromatic Rings 89
4.3 Transannulations with Ring Opening 90
4.3.1 Heteroaromatic Rings 90
4.3.2 Nonaromatic Rings 101
4.4 Summary and Outlook 110 References 111 5 Insertion of Azavinyl Carbenes to C--H/X--H Bond 115 Yury N. Kotovshchikov and Gennadij V. Latyshev
5.1 Abbreviations 115
5.2 Introduction 116
5.3 Insertion Reactions of N1-Sulfonyl-1,2,3-triazoles 116
5.3.1 C--H Insertion 116
5.3.2 O--H Insertion 133
5.3.3 N--H Insertion 149
5.3.4 B--H Insertion 154
5.3.5 Si--H and P--H Insertion 155
5.4 Insertion Reactions of 5-Iodo-1,2,3-triazoles 156
5.5 Summary and Outlook 160 Acknowledgment 160 References 160 6 Insertion of Azavinyl Carbenes to C--X/X--X Bond 171 Claire Empel and Rene M. Koenigs
6.1 Introduction 171
6.2 1,3-Difunctionalization 172
6.3 [2,3]-Sigmatropic Rearrangement Reactions 180
6.4 Insertion into X--X bonds 184
6.5 Conclusion 184 References 184 7 Denitrogenative Rearrangements of N -Sulfonyl-1,2,3-triazoles 189 Om Prakash Dash, Shivam Pandey, and Chandra M. R. Volla
7.1 Introduction to Carbenes 189
7.2 Metal Carbenoids 189
7.3 Metal Carbenoids Derived from Diazo Compounds 191
7.4 α-Imino Metal Carbenoids and Their Reactivity 191
7.5 Denitrogenative Rearrangements of N-Sulfonyl-1,2,3-triazoles Through Azadiene Formation 193
7.6 Denitrogenative Rearrangements of N-Sulfonyl-1,2,3-triazoles Through Zwitterionic Intermediate 200
7.7 Denitrogenative Rearrangements of N-Sulfonyl-1,2,3-triazoles Through Ylide Formation 201
7.8 Denitrogenative Rearrangements of N-Sulfonyl-1,2,3-triazoles Through Ketenimine Formation 206
7.9 Conclusion 207 Acknowledgments 208 References 208 8 Denitrogenative Transformations of NH- and N- Fluoroalkyl-1,2,3-triazoles211 Vladimir Motornov and Petr Beier
8.1 Introduction 211
8.2 Denitrogenation of NH-1,2,3-Triazoles 211
8.3 Denitrogenation of N-Fluoroalkyl-1,2,3-triazoles 218
8.4 Summary and Outlook 223 Acknowledgments 223 References 223 9 Asymmetric Perspective on Denitrogenative Transformation of 1,2,3-Triazoles 227 Pokhriyal Yamini, Akanksha Babbar, and Dongari Yadagiri
9.1 Introduction 227
9.2 Rhodium-Catalyzed Cyclopropanation Reactions 227
9.3 Rhodium-Catalyzed C--H Insertion Reactions 233
9.4 Rhodium-Catalyzed Transannulation Reactions 236
9.5 Miscellaneous Reactions 240
9.5.1 Relay Catalysis 240
9.5.2 Atom Transfer Reactions 242
9.6 Application in Natural Product and Total Synthesis 243
9.7 Summary and Outlook 246 Acknowledgments 246 References 246 10 Denitrogenative Transformations of 3-Diazoindolin-2-imines 251 Kavuri Rupa and Pazhamalai Anbarasan
10.1 Introduction 251
10.2 Synthesis of 3-Diazoindolin-2-imines 251
10.3 Insertion Reactions of 3-Diazoindolin-2-imines 253
10.3.1 Insertion into X--H Bonds 253
10.3.2 Insertion into C--H Bonds 255
10.3.3 Insertion into C--X Bonds 257
10.4 Annulation Reactions of 3-Diazoindolin-2-imines 260
10.5 Miscellaneous Reactions 271
10.6 Summary and Outlook 277 References 277 11 Metal-Catalyzed Denitrogenative Transformations of Pyridotriazoles 281 Deepa Rawat, Abhisek Joshi, and Subbarayappa Adimurthy
11.1 Introduction 281
11.2 Rhodium-Catalyzed Transannulation of Pyridotriazoles 283
11.2.1 Rhodium-Catalyzed Transannulation of Pyridotriazoles with Alkyl Silane, Alkynes, and Nitriles 283
11.2.2 Rhodium-Catalyzed Transannulation of Pyridotriazoles with Amine and Amides 287
11.2.3 Rhodium-Catalyzed [4 + 3] Cycloaddition of Pyridotriazoles with 2-Phenylpyridine and S-Aryl Sulfoximines 288
11.2.4 Rhodium-Catalyzed Transannulation of Pyridotriazoles with 1,3-Dienes 290
11.2.5 Rhodium-Catalyzed Transannulation of Pyridotriazoles with N- Phenylbenzimidamides 291
11.2.6 Rhodium-Catalyzed [4 + 1] Cycloaddition of Pyridotriazoles with Propargyl Alcohols 292
11.3 Palladium-Catalyzed Ring-Opening of [1,2,3]Triazolo [1,5-a]pyridines 293
11.3.1 Palladium-Catalyzed Ring-Opening of Pyridotriazole with Aryl Halides 294
11.3.2 Palladium-Catalyzed Ring-Opening of Pyridotriazole with Acetic Anhydride 297
11.4 Copper-Catalyzed Denitrogenative Transannulation of Pyridotriazoles 299
11.4.1 Copper-Catalyzed Transannulation of Pyridotriazoles with Alkynes 299
11.4.2 Copper-Catalyzed Transannulation of Pyridotriazoles with Amines and Amino Acids 300
11.5 Cobalt-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters 302
11.6 Ruthenium-Catalyzed Transannulation of Pyridotriazoles with Naphthoquinones 303
11.7 Summary and Conclusion 305 Acknowledgments 306 References 306 12 Metal-Free Denitrogenative Transformation of Pyridotriazoles 309 Sharma Happy, Akash Ratwan, and Dongari Yadagiri
12.1 Introduction 309
12.2 Acid-Catalyzed Denitrogenative Transformation of Pyridotriazoles 309
12.2.1 Lewis-Acid Catalyzed Reactions 309
12.2.2 Brønsted Acid-Catalyzed Reactions 312
12.3 Denitrogenative Transformations of Pyridotriazoles for Forming C--C and C--X Bond 315
12.3.1 Coupling of Boronic Acids with Pyridotriazoles 315
12.3.2 Iodine and Bromine Promoted Transformations of Pyridotriazoles 315
12.4 Thermolysis and Photolysis of Pyridotriazoles 316
12.5 Light-Induced Transformations of Pyridotriazoles 319
12.6 Summary and Outlook 321 Acknowledgments 321 References 321 13 Recent Development in Denitrogenative Transannulation of Benzotriazoles 325 Mangal S. Yadav, Manoj K. Jaiswal, Tanu Gupta, and Vinod K. Tiwari
13.1 Introduction 325
13.2 Common Route for the Synthesis of Benzotriazole Precursors 328
13.3 Transannulation of Benzotriazole-Appended Scaffolds 330
13.4 Conclusions and Future Perspective 349 Acknowledgments 350 References 350 14 Denitrogenative Transannulation of Thiadiazoles 359 Phil Ho Lee
14.1 Introduction 359
14.2 Rh-Catalyzed Reaction of 1,2,3-Thiadiazoles with Alkynes 359
14.2.1 Rh-Catalyzed Thiavinyl Carbenes from 1,2,3-Thiadiazoles for the Synthesis of Multisubstituted Thiophenes 359
14.2.2 Rh-Catalyzed Intramolecular Transannulation Reaction of Alkynyl Thiadiazoles for the Synthesis of 5,n-fused Thiophenes 361
14.2.3 Rh-Catalyzed Denitrogenative Transformations of 1,2,3-Thiadiazoles for the Synthesis of Multisubstituted Furans and Thiophenes 361
14.2.4 Rh-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization for the Synthesis of 4H-Thiopyran-4-