Chapter 1 reviews recent progress in aryne cycloaddition reactions.
The important contributions to the methodology of preparation of
arynes in mild reaction conditions are described. Among them, the
in-situ generation of arynes via the reaction of ortho- OTMS aryl
triflates with fluoride ions is the most applicable. By this
method, a variety of arynophiles was employed in the synthesis of
nitrogen and oxygen containing 5-7 membered heterocycles.
Instructive examples of applications in the total synthesis of
natural products (radermachol, (+/-)-tylophorine, calothrixins,
tubingensin B, (+)-hinckdentine A, cossonidine and
(methyl)teretifoliones B) are presented. The importance of
O-trimethylsilylaryl triflates and fluoride ions methodology for
aryne generation is demonstrated in preparation of bioactive
molecules and their applicability in medicinal chemistry research.
Chapter 2. In addition to thermal reactions, photocycloaddition
reactions are a complementary tool in synthetic organic chemistry.
The employment of photochemical cycloaddition reactions proceed
through different reaction mechanisms and provide access to
products which could not be obtained in classical reaction
conditions. This chapter is a review of excited state
transformations of heterostilbenes to polycyclic structures
featuring bicyclo[2.1.1], bicyclo[3.1.0] and bicyclo[3.2.1]
moieties. Alongside the main products of these types, often
unexpected transformations take place. Some of the
photocycloaddition products display interesting biological
activity. Chapter 3 reports the results of original scientific
research with regards to the application of click reactions in the
synthesis of 1,4-disubstituted 1,2,3-triazole conjugates with
ribofuranosides and reversed nucleosides. An efficient method for
the synthesis of 1,2,3-triazole bridged glycoconjugates with
potential biological activity is described and fully supported with
the 1H and 13C NMR spectroscopy of novel products. Chapter 4 is a
comprehensive review of isocyanide-based cycloaddition reactions.
This functionality is highly reactive and participates in many
different cycloaddition reactions and annulations. Employment of
isocyanide cycloaddition reactions led to the preparation of
diverse heterocyclic structures, including asymmetric ones and
their applications in medicinal chemistry, in the agricultural,
chemical, and supramolecular fields, as well as in the materials
sciences. Chapter 5 gives a review of the synthesis of
1,5-benzodiazepine-2,4-dione derivatives via 1,3-dipolar
cycloaddition reactions. Functionalization of
1,5-benzodiazepine-2,4-dione by the cycloadditions of nitrilimines,
nitrile oxides or azides led to diverse heterocyclic substitutions
at positions 1, 3 and 5. Molecular structures of novel products
were confirmed by X-ray crystal structure analyses. Chapter 6.
Nitrile imines, nitrile oxides and azides were employed in
1,3-dipolar cycloaddition reactions with allyl and propargyl
substituted 1,5-benzodiazepine, quinoxaline-2-thiones,
benzimidazole and isatin to afford derivatives with heterocylic
substituents: pyrazol, isoxazol and triazol. Single crystal X-ray
studies of novel products were described, and their biological
activity was also reported. Chapter 7. Guanidines are commonly
occurring in nature and constituents some natural products with
cyclic structures. Various cycloaddition reactions leading towards
cyclic guanidine structures were reviewed. The review also
summarized cycloaddition reactions in which functionalized
guanidines were acting as the reaction partners.
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