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Kikelj, D., Science of Synthesis, (2004) 16, 668.
2-Aryl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones undergo oxidative ring contraction with potassium permanganate in anhydrous acetone to give 2-arylquinazolin-4(3H)-ones in good yields (Scheme 143).[648] Since such ring contraction does not take place in the presence of manganese dioxide, this suggests that the reaction is aided by permanganate anion and proceeds via an intermediate 3-amino-2-arylquinazolin-4(3H)-one. 7-Chloro-5-phenyl-1,3,4-benzotriazepin-2-amines 215 undergo, on reflux in 5 M hydrochloric acid or 0.5 M ethanolic potassium hydroxide, a ring opening–ring closure reaction, resulting in overall ring contraction to 6-chloro-2-hydrazino-4-phenylquinazolines 216, which, on further heating, afford 6-chloro-4-phenylquinazolin-2(1H)-one (217) (Scheme 144).[649]
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References
[648] | Meeee, Me. M.; Meeee, M. M. M.; Meeeee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 888. |
[649] | Meeeeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 88.