Abstract
Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.
Highlights
Diazo compounds are incredibly useful reagents in synthetic organic chemistry due to their extremely versatile and unique reactivity [1,2,3,4,5]
A range of new methods have been developed for the synthesis of various heterocycles from diazo compounds, some of which are described in reviews [6,7,8,9,10,11,12]
Versatility and efficiency of diazo compounds are most clearly manifested in the synthesis of azoles—five-membered heterocycles containing a nitrogen atom and at least one other non-carbon atom of either nitrogen, oxygen, or sulfur
Summary
Diazo compounds are incredibly useful reagents in synthetic organic chemistry due to their extremely versatile and unique reactivity [1,2,3,4,5]. Diazo reagents allow synthesis of azoles of many types with two, three, and four heteroatoms These heterocycles have found broad application in many fields such as organic electronics, functional materials, explosives, dyes, fluorophores, and especially medicine. This review aims to summarize all recent developments in this area covering all types of azoles available from diazocarbonyl and related compounds (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, tetrazoles, with the exception of 1,2,3-thiadiazoles), as well as to consider earlier useful methodologies not mentioned in other reviews.
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