Advances in Heterocyclic Chemistry Volume 101

Advances in Heterocyclic Chemistry
 
Author:
Alan R. Katritzky
Release at: 2010
Pages: 244
Edition:
Volume 101
File Size: 10 MB
File Type: pdf
Language: English


Description of Advances in Heterocyclic Chemistry Volume 101


The final Volume 101 of Advances in Heterocyclic Chemistry celebrating the attainment of the century for AHC contains five chapters contributed by heterocyclic chemists from six countries. Soler, Moorefield, and Newkome (U. Akron, Akron, OH, USA) start with a fascinating account of the Senior Author’s work on the construction of hexameric macromolecular architectures in organic chemistry.

Patil, Kavthe, and Yamamoto (I.I.C.T., Hyderabad, India, and Tohoku U., Japan) summarize metal-catalyzed cyclizations of alkynes bearing a heteroatom attached to a substituent which migrates during the annulation. The chemistry of the 28 possible isomeric biindolyl structures is covered by Black and Kumar (UNSW, Sydney, Australia), while R.C.F. Jones (Loughborough U. Loughborough, UK) has reviewed his own and others’ research on annulation reactions of 2-imidazoline. The volume closes with an up to date account of the chemistry of the Dimroth Rearrangement contributed by E.S.H. El Ashry, S. Nadeem, M.R. Shah, and Y.E. Kilany of Alexandria U. in Egypt.

Content of Advances in Heterocyclic Chemistry Volume 101



CHAPTER 1
1. Introduction 2
2. Macrocycles with Five-Membered Heterocyclic Subunits 3
2.1 Furan, tetrahydrofuran, and thiophene 3
2.2 Pyrrole 6
2.3 Cucurbituril 18
2.4 Cyclofructans 19
2.5 Diazole 21
3. Six-Membered Ring Heterocycles 22
3.1 Pyridine 22
3.2 Pyrimidine 53
3.3 Phenanthroline 54
3.4 Oligosaccharides 56
4. Miscellaneous Heterocyclic Materials 58
4.1 Flexible rings 58
4.2 Terpyridine and phenanthroline 59
4.3 Five- and six-membered 60
4.4 Nucleobases, nucleosides, and nucleotides 64
5. Conclusions 66
References 66

CHAPTER 2
1. Introduction 75
2. Synthesis of O-Containing Heterocycles 76
3. Synthesis of N-Containing Heterocycles 83
4. Synthesis of S-Containing Heterocycles 89
5. Synthesis of Se-Containing Heterocycles 91
6. Conclusions 92
Acknowledgments 92
References 92

CHAPTER 3
1. Introduction 162
1.1 General schemes for type 1 163
1.2 General schemes for type 2 166
2. Translocation of Heteroatoms in Fused Heterocycles
(Type 1) 167
2.1 Rearrangement of pyrazoloheterocycles 167
2.2 Rearrangement of imidazoheterocycles 169
2.3 Rearrangement of 1,2,4-triazoloheterocycles 172
2.4 Rearrangement of 1,2,4-Triazinoheterocycles 181
3. Translocation of Exo- and Endocyclic Heteroatoms in
Heterocycles (Type 2) 181
3.1 Heterocycles with one heteroatom in the ring 182
3.2 Heterocycles with two heteroatoms in the ring 190
3.3 Heterocycles with three heteroatoms in the ring 217
3.4 Heterocycles with four heteroatoms in the ring 220
Acknowledgments 222
References 222

CHAPTER 4
1. Introduction 126
2. Polar Annulation Strategy 127
3. Imidazolines as Double Nucleophiles 128
3.1 Synthesis of substrates 128
3.2 Lateral metallation at C-2(a) 129
3.3 Enamine reactivity of the enamino ester 131
4. Annulations of the Enamino Ester/Ketene Aminal 132
4.1 Dihaloalkane electrophiles 132
4.2 a,b-Unsaturated aldehyde and ketone electrophiles 133
4.3 a,b-Unsaturated acid derivatives as electrophiles 134
4.4 1,3-Dicarbonyl compounds as electrophiles 136
5. Annulations of N-Unsubstituted 2-Imidazolines 137
5.1 a,b-Unsaturated aldehyde and ketone electrophiles 138
5.2 a,b-Unsaturated ester electrophiles 139
5.3 b-Keto esters as electrophiles 139
5.4 Diethyl acetylenedicarboxylate as electrophile 140
6. Imidazolines as Sources of 1,3-Dipoles 140
6.1 Synthesis of substrates 141
7. Azomethine Ylides by AlkylationDeprotonation 141
8. Azomethine Ylides by Carbene Insertion in a Catalytic
Cycle 146
9. Azomethine Ylides by Conjugate Addition-Proton
Transfer 147
9.1 Annulation via the conjugate addition route with
singly activated alkenes and with alkynes 149
10. Annulations Using Chiral Imidazolines 150
10.1 Synthesis of substrates 150

CHAPTER 5
1. Introduction 162
1.1 General schemes for type 1 163
1.2 General schemes for type 2 166
2. Translocation of Heteroatoms in Fused Heterocycles
(Type 1) 167
2.1 Rearrangement of pyrazoloheterocycles 167
2.2 Rearrangement of imidazoheterocycles 169
2.3 Rearrangement of 1,2,4-triazoloheterocycles 172
2.4 Rearrangement of 1,2,4-Triazinoheterocycles 181
3. Translocation of Exo- and Endocyclic Heteroatoms in
Heterocycles (Type 2) 181
3.1 Heterocycles with one heteroatom in the ring 182
3.2 Heterocycles with two heteroatoms in the ring 190
3.3 Heterocycles with three heteroatoms in the ring 217
3.4 Heterocycles with four heteroatoms in the ring 220
Acknowledgments 222
References 222


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