95721-09-8Relevant articles and documents
Annulation of the Quinazoline Ring Utilizing Mesoionic Ring Systems
Potts, Kevin T.,Bordeaux, Kirk G.,Kuehnling, William R.,Salsbury, Ronald L.
, p. 1666 - 1676 (2007/10/02)
anhydro-3-Hydroxythiazoloquinazolin-4-ium hydroxides, prepared from the corresponding thioglycolic acid with cyclodehydrating agents and also from 4(3H)-quinazolinethiones and α-bromophenylacetyl chloride, were hydrolyzed at the 5-position of the quinazoline ring with hot water.Alkynic and alkenic dipolarophiles cycloadded readily in hot benzene; the former gave pyridoquinazolines and the latter 1:1 cycloadducts which lost H2S to give the above ring system.These procedures provided convenient annulation of a pyridinone to the c side of quinazoline.With ethyl acrylate, in addition to the normal 1:1 cycloadduct, a rearranged pyrroloquinazoline was obtained depending on the reaction conditions; analogous products were obtained with dimethyl fumarate. anhydro-1-Hydroxythiazoloquinazolinium hydroxides, preferably generated in situ from the corresponding thioglycolic acid and dicyclohexylcarbodiimide (DCC), and alkynic dipolarophiles in refluxing benzene readily gave pyridoquinazolines.Alkenic dipolarophiles also gave 1:1 cycloadducts, which lost H2S to form pyridoquinazolines, resulting in annulation of a pyridinone ring to the a side of quinazoline.
