Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

Anton L. Shatsauskas; Sergey A. Kirnosov; Ekaterina S. Keyn; Vladislav Yu. Shuvalov; Anastasia S. Kostyuchenko; Alexander S. Fisyuk

doi:10.1055/a-2323-0770

Synthesis, Table of Contents

Synthesis 2024; 56(13): 2100-2108
DOI: 10.1055/a-2323-0770

paper

Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

Anton L. Shatsauskas

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

,

Sergey A. Kirnosov

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Ekaterina S. Keyn

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Vladislav Yu. Shuvalov

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

,

Anastasia S. Kostyuchenko

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

,

Alexander S. Fisyuk ∗

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

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Abstract

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Abstract

Two approaches were proposed for the synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones. The one-step method based on the Pictet–Spengler reaction of 3-amino-2-phenylquinolin-4(1H)-one with aromatic aldehydes requires heating in a strong acidic media, which leads to significant limitations on the possible products. The second approach is based on the conversion of 3-amino-2-phenylquinolin-4(1H)-one to 4-phenyl[1,3]oxazolo[4,5-c]quinolines followed by rearrangement under the action of AlCl₃. A significant advantage of the two-step synthesis is the possibility of obtaining a wider range of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones, including those not available using the Pictet–Spengler reaction.

Key words

heterocycles - rearrangement - Lewis acid - annulations - 1,5-naphthyridine - Pictet–Spengler reaction

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