Vicarious nucleophilic amination of nitroquinolines by 1,1,1‐trimethylhydrazinium iodide | Zendy

Grzegożek Maria | Zendy

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

Author(s) -

Grzegożek Maria

Publication year - 2008

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570450652

Subject(s) - chemistry , amination , iodide , nucleophile , yield (engineering) , medicinal chemistry , nitro , imine , hydrolysis , nucleophilic substitution , group (periodic table) , organic chemistry , catalysis , alkyl , materials science , metallurgy

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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