ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Substituted 2-Aminoquinoline-1-oxides by Reductive Cyclization of Substituted 3-(2-Nitrophenyl)acrylonitrilesAn approach to the class of 2-aminoquinoline-1-oxides is given based on reductive cyclization of appropriate substituted 3-(2-nitrophenyl)acrylonitriles. Thus, 2-nitrobenzylidene compounds 1 a - d have been reductively cyclized by H2/PtO2 or H2/Pd-C under normal conditions to form N-oxides 2 a - d. 1H-NMR data show that 1 d has to be regarded as ethyl(Z)-2-cyano-3-hydroxy-3(2-nitrophenyl)acrylate.The analogous (2-nitrobenzoyl)acetonitrile 3, however, did not cyclize under the same conditions, but yielded anthraniloylacetonitrile 4. The results are discussed in comparison with the reaction behaviour of structural related nitronitriles under comparable conditions. A short survey of reactions leading to heterocyclic N-oxides by reductive cyclization of nitro compounds is given.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19923340114
