Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates

[Display omitted] •Efficient synthesis of thiazolidin-4-ones.•[3+2] Cycloaddition reaction of aza-oxyallylic cations and isothiocyanates.•Easy operation, ambient temperature, good yields.•Broad functional group tolerance. A highly efficient one-pot synthesis of thiazolidin-4-ones via [3+2] cycloaddi...

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Bibliographic Details
Published in:Tetrahedron letters 2017-11, Vol.58 (45), p.4308-4311
Main Authors: Wang, Gangqiang, Zhao, Sen, Chen, Rongxing, Yang, Liangfeng, Wang, Jian, Guo, Haibing, Wu, Minghu, Domena, Justin, Xing, Yalan, Sun, Shaofa
Format: Article
Language:English
Subjects:
Aza-oxyallylic cation
Cycloaddition
Heterocycles
Isothiocyanates
One-pot
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Summary:[Display omitted] •Efficient synthesis of thiazolidin-4-ones.•[3+2] Cycloaddition reaction of aza-oxyallylic cations and isothiocyanates.•Easy operation, ambient temperature, good yields.•Broad functional group tolerance. A highly efficient one-pot synthesis of thiazolidin-4-ones via [3+2] cycloaddition of aza-oxyallylic cations with isothiocyanates is developed. The aza-oxyallyic cations were generated in situ in the present of a base. This cycloaddition reaction allows the rapid access to a variety of thiazolidin-4-one derivatives in mild conditions, good yield, and excellent functional group compatibility.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.10.004