Chemistry of Heterocyclic Compounds p. 511 - 514 (1982)
Update date:2022-08-04
Topics:
Shramm, N. I.
Konshin, M. E.
A substituted nicotinic acid is formed when 6-methyl-2-anilinonicotinonitrile is refluxed with concentrated hydrochloric acid, whereas 4,6-dimethyl-2-anilinonicotinonitrile is not hydrolyzed under these and more severe conditions because of steric hindrance.Both of these nitriles undergo cyclization to 10-aminobenzo-1,8-naphthyridine derivatives under the influence of concentrated sulfuric acid.When 6-methyl-2-arylaminonicotinonitriles are heated in polyphosphoric acid (PPA), they are converted to 2-arylaminonicotinic acid amides and, in part, to benzo-1,8-naphthyrid-10-one derivatives, while 4,6-dimethyl-2-arylaminonicotinonitriles are converted primarily to 10-aminobenzo-1,8-naphthyridines.
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Doi:10.1016/j.bmcl.2005.07.074
(2005)Doi:10.1016/j.tet.2004.10.030
(2004)Doi:10.1016/S0040-4039(00)87321-9
(1982)Doi:10.1039/d0sc01349h
(2020)Doi:10.1246/cl.1982.891
(1982)Doi:10.1246/cl.1982.875
(1982)
