HETEROCYCLIZATION OF 2-ACYL-3-INDOLYLACETIC ACIDS USING HYDRAZINE. SYNTHESIS OF 2,3-DIHYDRO-2-OXO-5-R1-1H-[1,2]DIAZEPINO[4,5-<i>b</i>]INDOLES

Authors

  • В. С. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 83114 Donetsk
  • А. Б. Ересько L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 83114 Donetsk
  • А. И. Хижан L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 83114 Donetsk
  • О. В. Шишкин STC Institute for Single Crystals, National Academy of Sciences of Ukraine, 61001 Kharkiv
  • Г. В. Паламарчук STC Institute for Single Crystals, National Academy of Sciences of Ukraine, 61001 Kharkiv
  • С. В. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 83114 Donetsk

DOI:

https://doi.org/10.1007/6698

Keywords:

2-aminoindolo[2, 3-c]pyridin-3(2H)-one, hydrazine hydrate, hydrazones of 2-acetyl-3-indolylacetic acid, 2, 3-dihydro-2-oxo-5-R1-1H-[1, 2]diazepino[4, 5-b]indoles

Abstract

The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does  not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate.

How to Cite
Tolkunov, V. S.; Eresko, A. B.; Khizhan, A. I.; Shishkin, O. V.; Palamarchuk, G. V.; Tolkunov, S. V.  Chem. Heterocycl. Compd. 2009, 45, 726. [Khim. Geterotsikl. Soedin. 2009, 907.]

For this article in the English edition see DOI 10.1007/s10593-009-0322-7


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Published

2022-03-24

Issue

No. 6 (2009)

Section

Original Papers