Derivatives of new condensed heterosystems, the tetracyclic [1,4]diazepino[3,2,1-hi]pyrido-[4,3,2-cd]indoles and tricyclic [1,4]diazepino[2,3-g]- and -[2,3-f]quinolines have been synthesized by the interaction of 7-amino-4-phenyl(or methyl)-1,3,4,5-tetrahydro(or 1,3-dihydro)-2H-1,5-benzodiazepin- 2-ones with dimethyl 2-oxoglutaconate and methyl 4-oxo-2-pentenoate. The corresponding carboxylic acids of the new derivatives were synthesized by alkaline hydrolysis of the methyl esters. The direction of the cyclocondensation reaction was determined by both the structure of the diazepine ring of the initial amines and also by the structure of the α,β-unsaturated ketones. Quantum-chemical calculations have been carried out of the minimal values of the local energy of ionization and of the resonance stabilization energy on specific atoms of the initial amines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1235-1244, August, 2010.
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Janciene, R., Stumbreviciute, Z., Vektariene, A. et al. Interaction of derivatives of 7-amino-1,5-benzo-diazepin-2-ones with α,β-unsaturated ketones. Chem Heterocycl Comp 46, 998–1005 (2010). https://doi.org/10.1007/s10593-010-0614-y
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DOI: https://doi.org/10.1007/s10593-010-0614-y