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Quinoline derivatives

I. Synthesis of quinoline derivatives via 1,2,3,4-tetrahydroquinoline

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of substituted tetrahydroquinolines were dehydrogenated for the first time to the corresponding quinoline derivatives by means of chloranil and a cupric chloride-pyridine complex. It is shown that the tendency for dehydrogenation decreases on passing from 6-formyl- to 6-bromo-, 6-nitro-, and 7-nitrotetrahydroquinolines. The nitration of N-acyltetrahydroquinolines (where the acyl group is formyl, acetyl, or benzoyl) was studied in detail. The possible formation of a 7-nitro isomer in addition to a 6-nitro isomer was demonstrated, and conditions which make it possible to vary the ratio of the yields of these isomers were found.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, USSR

    A. P. Terent'ev, I. G. Il'ina, L. G. Yudin, N. B. Kazennova & E. I. Levkoeva

Authors
  1. A. P. Terent'ev
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  2. I. G. Il'ina
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  3. L. G. Yudin
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  4. N. B. Kazennova
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  5. E. I. Levkoeva
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1663–1666, December, 1970.

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Terent'ev, A.P., Il'ina, I.G., Yudin, L.G. et al. Quinoline derivatives. Chem Heterocycl Compd 6, 1553–1556 (1970). https://doi.org/10.1007/BF00522580

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  • DOI: https://doi.org/10.1007/BF00522580

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