Synthesis of unsymmetrical dihydro triazine-2,4-diones by the N–N bond fragmentation of urazoles followed by intramolecular cyclization

[Display omitted] A new synthesis of unsymmetrical dihydro triazine-2,4- diones has been accomplished, through the strategy of a base-induced fragmentation of urazole derivatives, followed by an intramolecular cyclisation. Treating substituted urazole derivatives with LDA resulted in fragmentation o...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 106; p. 154076
Main Authors:	Panga, Subhaskar R., Hall, Roger G., Samant, Rashmi V., Montgomery, Mark, Shyadligeri, Ashok S.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 14-09-2022
Subjects:	Dihydro triazine-2,4-diones Fragmentation – cyclization N–N fragmentation Urazoles N–N fragmentation Urazoles Dihydro triazine-2,4-diones Fragmentation – cyclization
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Summary:	[Display omitted] A new synthesis of unsymmetrical dihydro triazine-2,4- diones has been accomplished, through the strategy of a base-induced fragmentation of urazole derivatives, followed by an intramolecular cyclisation. Treating substituted urazole derivatives with LDA resulted in fragmentation of the N–N bond generating an imine, which was trapped in an intramolecular fashion to give products in good to excellent yields. Features of this transformation include atom economy and a broad tolerance of aryl substituents. Where differentially substituted urazole derivatives are employed, only one dihydro triazine-2,4-dione isomer is obtained. We also demonstrate the transformation of such dihydro triazine-2,4-diones into triazine-2,4-diones and triazine-2,4,6-triones, enlarging the scope of this approach.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2022.154076