Efficient Preparation of Imidazo[1,5-a]pyridine-1-carboxylic Acids

Dmytro O. Tverdiy; Maksym O. Chekanov; Pavlo V. Savitskiy; Anatolii R. Syniugin; Sergiy M. Yarmoliuk; Andrey A. Fokin

doi:10.1055/s-0035-1561489

Synthesis, Table of Contents

Synthesis 2016; 48(23): 4269-4277
DOI: 10.1055/s-0035-1561489

paper

Efficient Preparation of Imidazo[1,5-a]pyridine-1-carboxylic Acids

Dmytro O. Tverdiy*

^aDepartment of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine Email: tverdiy_d@ukr.net

^bDepartment of Organic Chemistry, National Technical University of Ukraine ‘Kiev Polytechnic Institute’, 37 Peremohy Ave., 03056, Kiev, Ukraine

^cAzepine Ltd., Suite 7777, 6 Slington House, Rankine Road, Basingstoke, RG24 8PH, UK

,

Maksym O. Chekanov

^aDepartment of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine Email: tverdiy_d@ukr.net

,

Pavlo V. Savitskiy

^aDepartment of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine Email: tverdiy_d@ukr.net

,

Anatolii R. Syniugin

^aDepartment of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine Email: tverdiy_d@ukr.net

,

Sergiy M. Yarmoliuk

^aDepartment of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine Email: tverdiy_d@ukr.net

,

Andrey A. Fokin

^bDepartment of Organic Chemistry, National Technical University of Ukraine ‘Kiev Polytechnic Institute’, 37 Peremohy Ave., 03056, Kiev, Ukraine

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Abstract

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Abstract

We report a novel and efficient approach to the synthesis of imidazo[1,5-a]pyridine-1-carboxylic acids. By using the reaction of 2-(aminomethyl)pyridine with acyl chlorides followed by one-pot treatment with trifluoroacetic anhydride, 2,2,2-trifluoro-1-imidazo[1,5-a]pyridin-1-ylethanones were obtained, which were then converted into imidazo[1,5-a]pyridine-1-carboxylic acids in high preparative yields through haloform cleavage.

Key words

amides - cyclization - heterocycles - bicyclic compounds - acylation

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References

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