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Efficient and Chemoselective Procedure for Conversion of Rhodanine Derivatives into 1,3‐Thiazolidine‐2,4‐diones via 1,3‐Dipolar Cycloaddition Reaction and Rearrangement Sequences
Author(s) -
Roosta Atefeh,
Alizadeh Abdolali,
Rezaiyehraad Reze,
Khanpour Mojtaba
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003484
Subject(s) - thiazolidine , rhodanine , cycloaddition , nitrile , chemistry , molecule , combinatorial chemistry , proton nmr , 1,3 dipolar cycloaddition , stereochemistry , computational chemistry , organic chemistry , catalysis
Herein, we report a chemoselective 1,3‐dipolar cycloaddition reaction between 5‐alkylidene‐ or 5‐arylidene rhodanine derivatives and nitrile oxide generated in situ from dibromoformaldoxime to construct 1,3‐thiazolidine‐2,4‐dione scaffold under mild conditions. This strategy exhibits a distinguished manner to afford thiazolidine derivatives in a simple, rapid and practical route. The results proved that the reaction proceeds through an unpredictable rearrangement and no spirocyclic product is generated. The structures of the target molecules were confirmed by IR, 1 H NMR, 13 C NMR, mass spectra and unambiguously X‐ray crystal structure analysis.