Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Oleksandr O. Stepaniuk; Tymofii V. Rudenko; Bohdan V. Vashchenko; Vitalii O. Matvienko; Ivan S. Kondratov; Andrey A. Tolmachev; Oleksandr O. Grygorenko

doi:10.1055/s-0039-1707987

Synthesis, Table of Contents

Synthesis 2020; 52(13): 1915-1926
DOI: 10.1055/s-0039-1707987

paper

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Authors

Oleksandr O. Stepaniuk

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua
Tymofii V. Rudenko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua
Bohdan V. Vashchenko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua
Vitalii O. Matvienko

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net
Ivan S. Kondratov∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^сV. P. Kukhar Institute of Bioorganic Chemistry & Petrochemistry, NAS of Ukraine, Murmanska Street 1, Kyiv 02660, Ukraine
Andrey A. Tolmachev

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua
Oleksandr O. Grygorenko ∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: kondratov@mail.enamine.net

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua

Abstract

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Abstract

An efficient approach to the preparation of pyridine carboxylates fused with 5- or 6-membered heteroaromatic rings is described. The method relied on the Combes-type condensation of the low-molecular-weight β-alkoxyvinyl glyoxylates as CCC bis-electrophiles and with heteroaromatic amines as NCC binucleophiles. In most experiments, β-alkoxyvinyl glyoxylates without additional substituent at the β position led to the corresponding α-pyridine carboxylates (67–87% yield). In the case of β-methyl-substituted derivative, γ-pyridine carboxylates were obtained in 84–99% yield. It was found that regioselectivity of the condensation could be efficiently tuned by changing conditions, such as solvents and acidic additives (HOAc, DMSO or HCl–1,4-dioxane).

Key words

nitrogen heterocycles - fused pyridine - amino heterocycles - glyoxylates - condensation - regioselectivity

Full Text

References

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