[1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes

Elvira R Zaitseva; Dmitrii S Ivanov; Alexander Yu Smirnov; Andrey A Mikhaylov; Nadezhda S Baleeva; Mikhail S Baranov

doi:10.3390/molecules27165270

[1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes

Molecules. 2022 Aug 18;27(16):5270. doi: 10.3390/molecules27165270.

Authors

Elvira R Zaitseva¹, Dmitrii S Ivanov¹, Alexander Yu Smirnov^{1

2}, Andrey A Mikhaylov¹, Nadezhda S Baleeva^{1

2}, Mikhail S Baranov^{1

2}

Affiliations

¹ Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russia.
² Institute of Translational Medicine, Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997 Moscow, Russia.

Abstract

A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containing a difluoroboryl bridge in the dicarbonyl fragment of the molecule.

Keywords: 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate; BF3·Et2O; amides; debenzylation; nitrogen heterocycles.

MeSH terms

Carboxylic Acids
Cyclization
Quinolines*

Substances

Carboxylic Acids
Quinolines
1,2,3,4-tetrahydroquinoline

Grants and funding

20-73-10195/Russian Science Foundation