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Facile synthesis of model indazolo[2,1-c][1,3,4]benzotriazepine-5,13-diones.

  作者 Zahra, Jalal A.;El-Abadelah, Mustafa M.;Thaher, Bassam A.;Abu Laufer, Stefan;Boese, Roland;  
  选自 期刊  Heterocycles;  卷期  2008年75-12;  页码  2989-3004  
  关联知识点  
 

[摘要]In basic media, 2-aminobenzoates react with hydrazonoyl chlorides 2-HO2CC6H4NHN:CClCOR (R = Me, OMe; precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N'-(1-carboxyphenyl-2-amino)hydrazino]benzoates. In the presence of 1,1'-carbonyldiimidazole (CDI), the latter acyclic adducts undergo 2 consecutive lactamizations, involving both activated CO2H groups and the suitably located hydrazino-NH partners, to deliver the corresponding indazolo[2,1-c][1,3,4]benzotriazepin-5,13-diones. Structural assignments for these novel tetracyclic products are based on anal. and spectral (IR, MS, NMR) data, and confirmed by single-crystal x-ray structure detn. One of the compds. exhibited anticancer activity.

 
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