4-Aryloxy-2-phenylquinazolines

Pheuob -> aniliiies A new general method for conversion of phenols into anilines has been described by Scherrer and Beatty. A sodium phenoxide (prepared conveniently with sodium hydride) is condensed with 4-chloro-2-phenylquinazoline (I) at about 100° for 10 min. to give a 4-aryloxy-2-phenylquinazoline (2) in 70-85% yield. 

A peculiar method for synthesis of anilines that included as a key step the thermal rearrangement of 4-aryloxy-2-phenylquinazoline 228 to a 3-aryl-2-phenyl-4(3/f)quinazolinone 229 was described327 (equation 90). 

The S At reactivity of the quinazoline system offers synthetic applications for this heterocycle. For instance, 4-chloro-2-phenylquinazoline 30, by reaction with phenolates, is converted into the 4-(aryloxy)quinazoline 31. This undergoes a Chapman rearrangement at 300°C with a 1,3-migration of the aryl residue to N-3 forming the 3-arylquinazolin-4(3//)-one 32. The latter hydrolyses with aqueous acid to form benzoxazinone 33 and a primary arylamine ... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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