An Improved Synthesis of 1λ6,2,4,6‐Thiatriazine‐1,3,5‐trione Derivatives – the Sulfonimidamide‐featured Triazinones

N,N’‐dicarbamoylation of 4‐methylbenzenesulfon‐imidamide with carbonyldiimidazole, followed by a mono‐nucleophilic substitution with amines and subsequential ring closure in one‐pot, afforded 1λ6,2,4,6‐thiatriazine‐1,3,5‐trione derivatives in up to 83 % yields. The protocol also works well for aliph...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2022-06, Vol.7 (24), p.n/a
Main Authors: Chen, Yantao, Kollback, Johanna, Aurell, Carl‐Johan
Format: Article
Language:English
Subjects:
acylation
nucleophilic substitution
ring-closure
sulfonimidamides
triazinones
Online Access:Get full text
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Summary:N,N’‐dicarbamoylation of 4‐methylbenzenesulfon‐imidamide with carbonyldiimidazole, followed by a mono‐nucleophilic substitution with amines and subsequential ring closure in one‐pot, afforded 1λ6,2,4,6‐thiatriazine‐1,3,5‐trione derivatives in up to 83 % yields. The protocol also works well for aliphatic sulfonimidamides, such as methyl sulfonimidamide. The mechanism of formation of both desired and unexpected products is discussed. A novel one‐pot protocol to access sulfonimidamide‐featured triazinone derivatives from primary sulfonimidamides using CDI as the carbonyl source and easily accessible primary amines as the diversity component.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202201284