Journal
TETRAHEDRON LETTERS
Volume 54, Issue 35, Pages 4645-4648Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.06.053
Keywords
Heterocycles; Hydrazones; Hypervalent iodine; Nitrile imide; Tetrazines
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Funding
- Nanjing University of Science and Technology
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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. (C) 2013 Elsevier Ltd. All rights reserved.
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