4.5 Review

The Use of Electrophilic Cyclization for the Preparation of Condensed Heterocycles

Journal

SYNTHESIS-STUTTGART
Volume 53, Issue 19, Pages 3497-3512

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706036

Keywords

electrophilic cyclization; condensed heterocycles; heteroaryl alkenes; heteroaryl alkynes; bromine; iodine; arylsulfanyl chlorides

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This review focuses on the utility of electrophilic cyclization reactions in synthesizing various condensed heterocycles containing functional groups that can undergo further chemical transformations. It discusses the reactions of unsaturated derivatives of different heterocycles with electrophilic agents leading to annulation of partially saturated heterocycles, along with reaction conditions, mechanisms, and applications in organic synthesis. The review mainly covers research published since 2002 to establish the current state of the art in this area.
Condensed heterocycles are well-known for their excellent biological effects and they are undeniably important compounds in organic chemistry. Electrophilic cyclization reactions are widely used for the synthesis of mono-heterocyclic compounds. This review highlights the utility of electrophilic cyclization reactions as an effective generic tool for the synthesis of various condensed heterocycles containing functional groups that are able to undergo further chemical transformations, such as nucleophilic substitution, elimination, re-cyclization, cleavage, etc. This review describes the reactions of unsaturated derivatives of different heterocycles with various electrophilic agents (halogens, arylsulfanyl chlorides, mineral acids) resulting in annulation of an additional partially saturated heterocycle. The electrophilic reaction conditions, plausible mechanisms and the use of such transformations in organic synthesis are also discussed. The review mainly focuses on research published since 2002 in order to establish the current state of the art in this area.

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