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23.10.6.1.1 Method 1: Thermolysis of 1,2,3-Benzotriazin-4(3H)-ones

DOI: 10.1055/sos-SD-023-00342

Kollenz, G.Science of Synthesis, (200623372.

Thermal decomposition of 3-(benzylideneamino)-1,2,3-benzotriazin-4(3H)-ones 100 is a convenient procedure to obtain 2-arylquinazolin-4(3H)-ones 102 in yields of 5671% (Scheme 28).[‌53‌] Elimination of nitrogen gives 6-(oxomethylene)cyclohexa-2,4-dien-1-imine (101), which adds to the corresponding nitrile by a hetero-DielsAlder process (Scheme 28). This transient imidoylketene 101 is also capable of undergoing a cyclocondensation reaction with α-amino acids to afford 1,4-benzodiazepine-2,5-diones 103 in moderate yields.[‌54‌]

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