Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 30, Pages 8177-8181Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01166c
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Funding
- Shanghai Municipal Education Commission [14ZZ159]
- Natural Science Foundation of Shanghai [15ZR1418800]
- Shanghai Municipal Science and Technology Commission [12430501300]
- Shanghai Key Laboratory of Chemical Biology, Shanghai University of Engineering Science [14KY0415]
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Two classes of addition/cycloaddition cascade reactions of hydra-zinecarbodithioate (1) have been developed under mild reaction conditions. Reaction of hydrazinecarbodithioate (1) with form-aldehyde solution (2) and propiolic acid (3) gives 3-propargyl-5-thiol- 2,3-dihydro-1,3,4-thiadiazoles (5) via a decarboxylative coupling/cycloaddition domino sequence. When propiolic acid (3) is switched to phenyl boronic acid (4), a petasis/cycloaddition domino reaction is instead observed, in which 3-benzyl-5-thiol-2,3- dihydro-1,3,4-thiadiazoles (6) are obtained. Both these reactions show a wide range of functional-group compatibility for propiolic acids and aryl boronic acids, and give the corresponding products in moderate to good yields.
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