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Vicarious nucleophilic amination of nitroquinolines by 1,1,1-trimethylhydrazinium iodide

✍ Scribed by Maria Grzegożek


Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
201 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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The amination of 3‐, 5‐, 6‐, 7‐ and 8‐nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1‐trimethylhydrazinium iodide (TMHI) in the presence of t‐BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95‐86%). 2‐Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives2(1__H__)‐quinolinone.


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