ANOMALOUS BECKMANN REACTION OF 4-ARYL-2,7,7-TRIMETHYL-5-OXO-5,6,7,8-TETRAHYDROQUINOLINE OXIMES IN POLYPHOSPHORIC ACID. 1. NEW SYNTHESIS OF 1-ETHOXYCARBONYL-2,5,5-TRIMETHYL-5,6-DIHYDRO-4H-PYRIDO[2,3,4-<i>k</i>,<i>l</i>]ACRIDINES

Authors

  • С. В. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of the Ukraine, Donetsk 83114
  • А. И. Хижан L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of the Ukraine, Donetsk 83114
  • В. И. Дуленко L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of the Ukraine, Donetsk 83114

Keywords:

4-aryl-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinolines, 1-ethoxycarbonyl-2,5,5-trimethyl-5,6-dihydro-4H-pyrido[2,3,4,-k,l]acridines, Semmler–Wolff aromatization, Beckmann rearrangement

Abstract

Transformations of oximes of 4-aryl-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinolines in PPA have been studied. It is shown that the reaction, depending on substituent at position 4 of quinoline ring, can occur in three directions: aromatization of the saturated ring (Semmler–Wolff aromatization), formation of azepinones – normal products of Beckmann rearrangement, and formation of pyridoacridines.

How to Cite
Tolkunov, S. V.; Khyzhan, A. I.; Dulenko, V. I. Chem. Heterocycl. Compd. 2003, 39, 1627. [Khim. Geterotsikl. Soedin. 2003, 1849.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000018341.97883.c0

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Published

2003-12-25

Issue

No. 12 (2003)

Section

Original Papers