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A new polycyclic system containing the 1,4-benzodiazepine and isoindolinone fragments: synthesis and structure

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Dehydration of 2-(3,3-dimethyl-1-oxo-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]-diazepin-11-yl)benzoic acid (3a) and 2-(3,3-dimethyl-1-oxo-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e] [1,4]diazepin-11-yl)-5,6-dimethoxybenzoic acid (3b) in boiling acetic or propionic anhydride gave 7,7-dimethyl-4b,7,8,9-tetrahydro-6H-dibenzo[2,3:5,6][1,4]diazepino[7,1-a]-isoindole-5,15-dione (5a) and 1,2-dimethoxy-7,7-dimethyl-4b,7,8,9-tetrahydro-6H-dibenzo-[2,3:5,6][1,4]diazepino[7,1-a]isoindole-5,15-dione (5b), respectively. The products obtained are representatives of a novel fused pentacyclic system. The structures of compounds 3b and 5a were unambiguously proved by X-ray diffraction.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    L. Yu. Ukhin, L. V. Belousova, Zh. I. Orlova & G. S. Borodkin

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitskii

  3. Southern Scientific Center of the Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov-on-Don, Russian Federation

    E. N. Shepelenko

Authors
  1. L. Yu. Ukhin
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  2. K. Yu. Suponitskii
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  3. E. N. Shepelenko
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  4. L. V. Belousova
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  5. Zh. I. Orlova
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  6. G. S. Borodkin
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Corresponding author

Correspondence to L. Yu. Ukhin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1703–1707, August, 2011.

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Ukhin, L.Y., Suponitskii, K.Y., Shepelenko, E.N. et al. A new polycyclic system containing the 1,4-benzodiazepine and isoindolinone fragments: synthesis and structure. Russ Chem Bull 60, 1729–1733 (2011). https://doi.org/10.1007/s11172-011-0258-9

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  • DOI: https://doi.org/10.1007/s11172-011-0258-9

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