Of 4-chloro-2-phenylquinazoline

Quinazolines take part in the same types of reactions as pyrimidines, but because of their additional benzene ring, the products of these reactions may have the added feature of hindered rotation. An example of this is the synthesis of 2-phenyl-Quinazolinap by Guiry and co-workers <99TA2797>. Suzuki coupling of 4-chloro-2-phenylquinazoline (115) with boronic acids 116 led to 117 (R = OMe). These intermediates were parlayed into phosphinamines 117 (R = PPh2) and then subjected to chiral resolution to produce new chiral phosphinamine ligands for asymmetric catalysis. 

Selective nitrogen labell ing experiments may also provide a good means of elucidating certain reaction mechanisms. The reaction of 4-chloro-2-phenylquinazoline with labelled potassium azide was shown to lead to tautomer species. A, B, in which the position of the label is easily identified. Thus, in trifluoroacetic acid solution, the azide tautomers of type B... 

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