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Paper | Regular issue | Vol 75, No. 12, 2008, pp.2989-3004
Published online, 10th July, 2008
DOI: 10.3987/COM-08-11464
Facile Synthesis of Model Indazolo[2,1-c][1,3,4]benzotriazepin-5,13-diones

Jalal A. Zahra, Mustafa M. El-Abadelah,* Bassam A. Abu Thaher, Stefan Laufer, and Roland Boes

*Chemistry Department, Faculty of Science, University of Jordan, Amman, Jordan

Abstract

In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N’-(1-carboxyphenyl-2-amino)hydrazino]benzoic acids (8a-d, 9a). The latter acyclic adducts, in the presence of 1,1‘-carbonyldiimidazole (CDI), undergo two consecutive lactamizations involving both activated carboxyl groups and the suitably located hydrazino-NH partners, to deliver the respective indazolo[2,1-c]- [1,3,4]benzotriazepin- 5,13-diones (10a-d, 11a). Structural assignments for these novel tetracyclic products are based on analytical and spectral (IR, MS, NMR) data, and confirmed by single crystal X-ray structure determination for 10a.