Thioalkynes in Ring Forming Reactions

Organic cycles play an important role in chemistry, pharmacology and material science for their unique properties. Construction of organic cycles from thioalkynes attracted increasing attention due to the facile access of thioalkynes. 2H-Azirines were synthesized successfully from thioalkynyl oxime ethers. Cyclobutanes were formed through chiral titanium catalyzed cycloaddition of thioalkynes. Cyclopentenes were afforded by annulation of thioalkynes. Thioalkynes could be also applied to synthesize thiophenes, oxazoles, benzo[b]thiophenes, 2H-chromenes, 2-phenylbenzothiazoles, diazacyclobutene, etc. In this review, construction of organic cycles from thioalkynes were highlighted. Firstly, the property and application of organic cyclic compounds were simply introduced. After presenting the general methods to access organic cycles, applications of thioalkynes as synthons to prepare organic cycles were classified and presented in detail. Based on different kinds of organic cycles obtained from thioalkynes, organic reactions for synthesis of three-, four-, five-, six-membered as well as fused cycles would be summarized and the plausible reaction mechanisms could be presented if available.

Automated summary

Organic cycles are important in chemistry, pharmacology, and material science due to their unique properties. Thioalkynes have attracted increasing attention as a convenient source for constructing organic cycles. This review highlights the construction of organic cycles from thioalkynes, including the synthesis of 2H-azirines, cyclobutanes, and cyclopentenes. Thioalkynes can also be used to synthesize various other cyclic compounds. The review provides an overview of the methods for accessing organic cycles and presents detailed applications of thioalkynes as synthons for preparing organic cycles, with a focus on different types of organic cycles and their corresponding reaction mechanisms if available.