An efficient method for accessing carboannulated and functionalized [1,2,3]triazolo[4,5- b ]pyridines
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An efficient method for accessing carboannulated and functionalized [1,2,3]triazolo[4,5-b]pyridines Natalia А. Syrota1*, Sergiy V. Kemskiy2, Andriy V. Bol'but2,3, Igor I. Chernobaev2, Mikhailo V. Vovk2 1
National University ''Kyiv-Mohyla Academy'', 2 Hrygorija Skovorody St., Kiev 04655, Ukraine; e-mail: [email protected] 2 Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine; e-mail: [email protected] 3 Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094, Ukraine; e-mail: [email protected] Submitted March 2, 2020 Accepted after revision June 3, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 1048–1053
4-(N-Boc-amino)-1,2,3-triazole-5-carbaldehydes upon heating under reflux in acetic acid in the presence of pyrrolidine react with cycloalkanones, acetylacetone, 1,3-cyclohexanediones, and malononitrile resulting in annulation of the pyridine ring with the formation of new derivatives of [1,2,3]triazolo[4,5-b]pyridine. Keywords: acetylacetone, 4-(N-Boc-amino)-1,2,3-triazole-5-carbaldehydes, 4-(N-Boc-amino)-1,2,3-triazoles, cycloalkanones, 1,3-cyclohexanediones, malononitrile, [1,2,3]triazolo[4,5-b]pyridine derivatives, annulation.
The [1,2,3]triazolo[4,5-b]pyridine system is a valuable molecular scaffold that has been widely used in the past few years in the search for biologically active compounds. Usually, their design is based on the structural modification of the triazole or pyridine rings. As a result, various 1-substituted [1,2,3]triazolo[4,5-b]pyridines were synthesized, among which selective inhibitors of phosphodiesterase (PDE10),1 lipases and phospholipases,2 human monoacylglycerol lipase (hMAGL),3 hydrolases of fatty acid amides,4 tubulin polymerase,5 S-adenosyl homocysteine hydrolase,6 acid ceramidase,7 C-chemokine receptor 9 (CCR-9),8 agonists of the farnesoid receptor (FXR)9 have been found. Their pyridine-functionalized 0009-3122/20/56(8)-1048©2020 Springer Science+Business Media, LLC
derivatives are equally important, some of which are pesticides,10,11 potential agents for the treatment of metabolic diseases,12 inhibitors of the Janus kinase,13 neutral endopeptidase,14 poly (ADP-ribose) polymerase (PAPR),15 myeloperoxidase,16 as well as modulators of the tyrosine kinase receptor.17 The known methods for the synthesis of [1,2,3]triazolo[4,5-b]pyridine derivatives are based on annulation of the triazole ring to the pyridine ring, which is usually performed by diazotization of 2,3-diaminopyridines5,14–16,18–20 or their N-substituted analogs.7,8,10,11,21–23 Moreover, the methods for the preparation of diamines containing functional substituents in the pyridine ring10–15 are usually
1048
Chemistry of Heterocyclic Compounds 2020, 56(8), 1048–1053 Scheme 1
multistep, are characterized by mediocre yields, and often involve chromatographic purification. For this reason, it seemed appropriate to develop an alternative method of obtaining new derivatives of [1,2,3]triazolo[4,5-b]pyridine involving annulation of the pyridi
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