Synthesis 2020; 52(13): 1915-1926
DOI: 10.1055/s-0039-1707987
paper
© Georg Thieme Verlag Stuttgart · New York

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

Oleksandr O. Stepaniuk
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
b   Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine   Email: gregor@univ.kiev.ua
,
Tymofii V. Rudenko
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
b   Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine   Email: gregor@univ.kiev.ua
,
Bohdan V. Vashchenko
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
b   Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine   Email: gregor@univ.kiev.ua
,
Vitalii O. Matvienko
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
,
Ivan S. Kondratov
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
с   V. P. Kukhar Institute of Bioorganic Chemistry & Petrochemistry, NAS of Ukraine, Murmanska Street 1, Kyiv 02660, Ukraine
,
Andrey A. Tolmachev
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
b   Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine   Email: gregor@univ.kiev.ua
,
a   Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: kondratov@mail.enamine.net
b   Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine   Email: gregor@univ.kiev.ua
› Author Affiliations
The work was funded by Enamine Ltd.; O.O.G. was also funded by Ministry of Education and Science of Ukraine (Grant No. 19BF037-03).
Further Information

Publication History

Received: 03 February 2020

Accepted: 15 February 2020

Publication Date:
12 March 2020 (online)


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).

Supporting Information

 
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