A Mechanistic Approach to Liquid‐Assisted Mechanochemical Synthesis of 5‐Aryl/Spiro‐[1,2,4]‐triazolidine‐3‐thiones

1,3‐dimethylbarbituric acid‐H2O mediated liquid assisted mechanochemical route has been developed for the synthesis of a wide array of 5‐aryl/spiro‐1,2,4‐triazolidine‐3‐thiones, via in situ generation of benzylidene/alkylidene barbiturates, followed by tandem, base‐driven Michael addition reaction a...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-09, Vol.2022 (34), p.n/a
Main Authors: Dutta, Anurag, Abha Saikia, Raktim, Jyoti Thakur, Ashim
Format: Article
Language:English
Subjects:
Alkylidene
Aromatic compounds
Domino reactions
Mechanochemistry
Michael reaction
Multicomponent reactions
Reaction mechanisms
Room temperature
Synthetic methods
Triazolidines
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Summary:1,3‐dimethylbarbituric acid‐H2O mediated liquid assisted mechanochemical route has been developed for the synthesis of a wide array of 5‐aryl/spiro‐1,2,4‐triazolidine‐3‐thiones, via in situ generation of benzylidene/alkylidene barbiturates, followed by tandem, base‐driven Michael addition reaction and rearrangement of the pyrimido[4,5‐e][1,2,4]triazepine intermediate. The method is an application of mechanochemistry in organic synthesis. It is efficient, easy to follow and avoids the tedious steps of catalyst preparation and chromatographic separation. Moreover, the protocol is compared to “on‐water”, room temperature approach and the reaction mechanism has been revisited with the aid of experiments. Room temperature, Liquid assisted grinding was used for the synthesis 5‐aryl/spiro‐[1,2,4]‐triazolidine‐3‐thiones. This protocol is a catalyst‐free and atom economic process bearing wide substrate scope and the isolation of products is chromatography free. It shows an efficient application of mechanochemical synthesis and also exemplifies green chemistry.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101472