A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines

Nucleophilic displacement of chlorides in 3,3′-dichloro-5,5′-bi-1,2,4-triazine with benzenethiolate or 2-pyridinethiolate anion afforded the corresponding symmetrical disulfide of 5,5′-bi-1,2,4-triazine in high yields. These products were transformed into 6,6′-bis(phenylthio)-2,2′-bipyridines and 6,...

Full description

Saved in:
Bibliographic Details
Published inHeterocyclic communications Vol. 20; no. 1; pp. 5 - 9
Main Authors Ławecka, Justyna, Olender, Ewa, Karczmarzyk, Zbigniew, Wysocki, Waldemar, Branowska, Danuta, Urbańczyk-Lipkowska, Zofia, Kalicki, Przemysław
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.02.2014
Walter de Gruyter GmbH
Subjects
2-pyridinethiol
5,5′-bi-1,2,4-triazine
C-S bond
Diels-Alder reaction
nucleophilic substitution
organic sulfides
X-ray analysis
Online AccessGet full text

Cover

More Information
Summary:Nucleophilic displacement of chlorides in 3,3′-dichloro-5,5′-bi-1,2,4-triazine with benzenethiolate or 2-pyridinethiolate anion afforded the corresponding symmetrical disulfide of 5,5′-bi-1,2,4-triazine in high yields. These products were transformed into 6,6′-bis(phenylthio)-2,2′-bipyridines and 6,6′-bis(2-pyridylthio)-2,2′-bipyridines by using Diels-Alder reactions. All compounds were fully characterized by spectroscopic methods and the X-ray diffraction analysis.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2013-0214