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Benzenoid-quinoid tautomerism of azomethines and their structural analogs. 42. Synthesis, structures, and spectral-luminescence properties of 3-hydroxy-2-acetylbenzo[b]thiophene imines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

N-Aryl- and N-alkylimines of 3-hydroxy-2-acetylbenzo[b]-thiophene, the most stable isomeric form of which, according to the UV, IR, and 1H NMR spectra data, is the E-keto enamine structure, were synthesized. Irradiation of the aminovinyl ketones in the region of the long-wave absorption band causes thermally and photochemically reversible E⇄Z isomerization. 2-Aminoethylidene-3-(2H)-benzo[b]thiophenones have low-intensity fluorescence with a normal Stokesian shift, which is absent in solutions of their lithium and sodium salts.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, M. A. Suslov Rostov State University, 344104, Rostov-on-Don

    E. N. Shepelenko, V. A. Bren', A. D. Dubonosov, A. É. Lyubarskaya & V. I. Minkin

Authors
  1. E. N. Shepelenko
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  2. V. A. Bren'
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  3. A. D. Dubonosov
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  4. A. É. Lyubarskaya
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  5. V. I. Minkin
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Additional information

See [1] for Communication 41.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 591–595, May, 1989.

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Shepelenko, E.N., Bren', V.A., Dubonosov, A.D. et al. Benzenoid-quinoid tautomerism of azomethines and their structural analogs. 42. Synthesis, structures, and spectral-luminescence properties of 3-hydroxy-2-acetylbenzo[b]thiophene imines. Chem Heterocycl Compd 25, 489–493 (1989). https://doi.org/10.1007/BF00482489

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  • DOI: https://doi.org/10.1007/BF00482489

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