Abstract
6-Allyloxy-9-benzylpurine ( 2 ) and 9-benzyl-6-propargyloxy purine ( 5 ) undergo normal thermal O→N [3,3] rearrangement, either neat or in o-dichlorobenzene. The latter leads to the novel, 1-allenyl-9-benzyl-hypoxanthine ( 6 ). The related 4-allyloxy and 4-propargyloxy quinazoline; ( 9 , 12 ) also undergo smooth thermal O→N Claisen rearrangement. In the case of( 12 ), the primary allenic product is further transformed into 3-propargylquinazolin-4-one ( 13 ) and the allene dimer ( 14 ).
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