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

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

Publication History

Received: 01 April 2024

Accepted after revision: 10 May 2024

Accepted Manuscript online:
10 May 2024

Article published online:
28 May 2024

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