CONDENSED PYRIDINE BASES. SYNTHESIS AND REACTIONS OF BENZOFURO[2,3-<i>c</i>]INDENO[2,1-<i>e</i>]-, BENZOTHIENO[2,3-<i>c</i>]INDENO[2,1-<i>e</i>]-, BENZOFURO[3,2-<i>c</i>]INDENO[2,1-<i>e</i>]- AND THIENO[2,3:4',5']THIENO[3,2-<i>c</i>]INDENO[2,1-<i>e</i>]PYRIDINES

Authors

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

DOI:

https://doi.org/10.1007/8354

Keywords:

benzo[b]thiophene, benzo[b]furan, indeno[2, 1-e]pyridines, pyrilium salts, thieno[2, 3-b]thiophene, condensation

Abstract

Condensation of hetarene carboxaldehydes with phthalide gave 2-(3-hydroxy-1-oxoinden-2-yl)benzo[b]furan and 2-(3-hydroxy-1-oxoinden-2-yl)-5-ethylthieno[2,3-b]thiophene. Starting from hetaryl acetic acids gave 3-(3-hydroxy-1-oxoinden-2-yl)benzo[b]furan and 3-(3-hydroxy-1-oxoinden-2-yl)benzo[b]thiophene. Acylation of 3-hydroxy-1-oxoinden-2-yl-substituted heterocycles using acetic anhydride in the presence of 70% HClO4 leads to the formation of pentacyclic pyrilium salts. Pentacyclic indenopyridines are prepared by treating the pyrilium salts with ammonia. The reaction of the carbonyl group in the indenopyridines with hydroxylamine, hydrazine hydrate, and in reduction using NaBH4 has been studied.

How to Cite
Tolkunov, S. V.; Khyzhan, A. I.; Suikov, S. Yu.; Dulenko, V. I. Chem. Heterocycl. Compd. 2005, 41, 379. [Khim. Geterotsikl. Soedin. 2005, 435.]

For this article in the English edition, see DOI 10.1007/s10593-005-0158-8


Published

2023-11-29

Issue

No. 3 (2005)

Section

Original Papers