Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene

A mild and efficient protocol for the construction of 1,4-dihydro-3,6-disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good t...

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Bibliographic Details
Published in:Tetrahedron letters 2013-08, Vol.54 (35), p.4645-4648
Main Authors: Liu, Haixuan, Wei, Yunyang
Format: Article
Language:English
Subjects:
Construction
Derivatives
Fluorides
Heterocycles
Hydrazones
Hypervalent iodine
Nitrile imide
Pyridines
Synthesis (chemistry)
Tetrabutyls
Tetrahedrons
Tetrazines
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Summary:A mild and efficient protocol for the construction of 1,4-dihydro-3,6-disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good to excellent yields. The corresponding 3,6-disubstituted-1,2,4,5-tetrazines can be easily obtained through one-step N-deprotection of p-toluensulfonyl groups and aromatization by tetrabutyl ammonium fluoride in THF. A mechanism has been proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.06.053