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DIMROTH REARRANGEMENT IN THE SYNTHESIS OF SUBSTITUTED CYCLOPENTA- AND CYCLOHEXA[4,5]THIENO[2',3':4,5]PYRIMIDO[1,6-b][1,2,4]TRIAZINES

Дмитрий О. Коломейцев, Виктор И. Марков, Светлана А. Варениченко, Валерия О. Астахина, Сергей И. Коваленко, Александр В. Харченко, Александр В. Мазепа
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Abstract


A simple and effective method has been developed for the synthesis of previously unknown cyclopenta- and cyclohexa[4',5']thieno-[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines in a single step by reaction of 4-hydrazinocyclopenta- and 4-hydrazinocyclohexa[4,5]thieno[2,3-d]pyrimidines with sodium salts of methyl 4-aryl(heteryl)-2,4-dioxobutanoates. It was shown that the determining factor in the formation of tetracyclic products was isomerization by intramolecular recyclization with mechanism analogous to the Dimroth rearrangement.

Authors: Dmitriy O. Kolomeitsev, Viktor I. Markov, Svetlana A. Varenichenko*, Valeriya O. Astakhina,
Sergiy I. Kovalenko, Olexander V. Kharchenko, Aleksandr V. Mazepa


Keywords


2,4-diketoesters; thieno[2,3-d]pyrimidines; thieno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines; Dimroth reaction mechanism; heterocyclization

Full Text: PDF (Russian) Supplementary File(s): Supporting information (1MB)


 

 

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