Synthesis 2023; 55(08): 1267-1273
DOI: 10.1055/a-1993-3714
paper

Easy Route to New Fused Dihydroisoquinoline-Naphthyridinone Frameworks

Vladislav Yu. Shuvalov
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation
,
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave., 644077 Omsk, Russian Federation
› Author Affiliations

This work was supported by the Russian Science Foundation (grant No. 22-13-00356).


Abstract

The reaction of 1-methyl-3,4-dihydroisoquinolines with azlactone, obtained from hippuric acid and phthalic anhydride, provided 2-(3-benzamido-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-2-yl)benzoic acids, which were converted into previously unknown dihydroisoquinoline-naphthyridinones by the action of hydrazine hydrate. Further reaction of the prepared naphthyridine-5,7-diones with POCl3 under various conditions led to the formation of 5-chloro-9,10-dihydro-7H-benzo[c]isoquinolino[1,2-g][1,7]naphthyridin-7-ones or 4,6-dichloro-2-(2-(2-methylprop-1-en-1-yl)phenyl)benzo[c][1,7]naphthyridines. It was also shown that the halogen atom in the C-5 position enters into a substitution reaction with primary and secondary amines.

Supporting Information



Publication History

Received: 28 October 2022

Accepted: 06 December 2022

Accepted Manuscript online:
06 December 2022

Article published online:
04 January 2023

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