SYNTHESIS OF 6-R-5-ARYL-1,3-DIOXO-1,2,3,4-TETRAHYDRO[1]BENZOTHIENO[3',2':4,5]PYRIDO[2,3-<i>d</i>]PYRIMIDIN-5-IUM SALTS AND 6-R-5-ARYL-5,6-DIHYDRO[1]BENZOTHIENO[3',2':4,5]PYRIDO[2,3-<i>d</i>]PYRIMIDINE-1,3(2<i>H</i>,4<i>H</i>)-DIONES

Authors

  • В. С. Толкунов L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine
  • А. Б. Ересько L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine
  • А. В. Мазепа A. V. Bogatsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine
  • С. В. Толкунов L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/383

Keywords:

benzothiophen-3(2H)-one, 5-(benzothiophen-3-yl)pyrimidine-2, 4, 6(1H, 3H, 5H)-trione, pyrilium salts, pyrimidine-2, 6-R-5-aryl-1, 3-dioxo-1, 2, 3, 4-tetrahydro[1]benzothieno[3', 2', 5]pyrido[2, 3-d]pyrimidin-5-ium chlorides, acylation, reduction

Abstract

Acylation of 5-(benzothiophen-3-yl)pyrimidine-2,4,6(1H,3H,5H)-trione using acetic and propionic anhydride in the presence of 70% perchloric acid gave the 6-methyl(ethyl)-1,3-dioxo-1,2,3,4-tetra-hydro[1]benzothieno[3',2':4,5]pyrano[2,3-d]pyrimidin-5-ium perchlorates. Hydrolysis of the pyrano[2,3-d]pyrimidin-5-ium salts in aqueous alcohol solution gave 5-(2-acylbenzothiophen-3-yl)-pyrimidine-2,4,6(1H,3H,5H)-triones. Cyclocondensation of the latter with aromatic amine hydrochlorides produced 6-R-5-aryl-1,3-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3',2':4,5]pyrido[2,3-d]-pyrimidin-5-ium chlorides. 6-R-5-Aryl-5,6-dihydro[1]benzothieno[3',2':4,5]pyrido[2,3-d]pyrimidine-1,3(2H,4H)-diones were synthesized by reduction of the pyrimidinium chlorides using sodium borohydride.

Authors: V. S. Tolkunov, A. B. Eresko, A. V. Mazepa, and S. V. Tolkunov.

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (6), pp 941-948

http://link.springer.com/article/10.1007/s10593-013-1329-7

Author Biographies

В. С. Толкунов, L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine

Валерий Сергеевич Толкунов, кандидат химических наук, старший научный сотрудник, отдел хими биологически активных соединений

А. Б. Ересько, L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine

Александр Борисович Ереско, младший научный сотрудник,  отдел хими биологически активных соединений

А. В. Мазепа, A. V. Bogatsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine

Александр Владимирович Мазепа, кандидат химических наук, старший научный сотрудник

С. В. Толкунов, L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine

Сергей Владимирович Толкунов, доктор химических наук, ведущий научный сотрудник, Отдел химии биологически активных соединений

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Published

2013-06-13

Issue

No. 6 (2013)

Section

Original Papers