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2005
Multi-membered N-heterocycles
R 0690
Synthesis of 1,4-Benzodiazepine-3,5-diones. — Several title compounds are formed
cyclization of N-carbamoylmethylanthranilic acids under treatment with chloro04- 176 by
formate and triethylamine. For the success of the reaction, it is necessary that electron-withdrawing substituents are present at the anthranilic nitrogen. This is achieved
either by in situ N-acylation or by N-nitrosated anthranilic acids. Benzodiazepines, obtained by the latter method, are denitrosated under acidic conditions as exemplified on
compound (X), or under reductive conditions, exemplified on compound (XIII). In addition, a novel ring contraction rearrangement of compound (X) to quinazolinone (XV)
is observed. — (WIKLUND, P.; ROGERS-EVANS, M.; BERGMAN*, J.; J. Org.
Chem. 69 (2004) 19, 6371-6376; Unit Org. Chem., CNT, Dep. Biosci. Novum,
Karolinska Inst., S-141 57 Huddinge, Swed.; Eng.) — Klein
2005
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