Synthesis of novel benzo naphtho naphthyridines from 2,4‐dicloroquinolines

Abstract

A schematic study on the condensation of 2,4‐dichloroquinolines (1) with 1‐naphthyamine (2) in the presence of CuI as a catalyst to functionalized mono (3) and di (4) substituted naphthylamino quinolines was described. Consequently, these mono‐ and di‐substituted amines on polyphosphoric acid‐catalyzed cyclization reaction with p‐toluic acid and acetic acid to yield the linear benzo[b]naphtho[2,1‐g][1,8]naphthyridines (5) and angular benzo[b]naphtho[2,1‐h] naphthyridines (6) in good yields. In addition to descried the similar synthesis of benzo[g]naphtho [2,1‐b][1,8]naphthyridines (12) and benzo[h]naphtho[2,1‐g][1,8]naphthyridines (13) from 2,4‐dichlorobenzo[h]quinoline (8) with various anilines (9) through my intermediates (10 and 11).

Enhanced Method for the Synthesis and Comprehensive Characterization of 1-(4-Phenylquinolin-2-yl)propan-1-one

“…Based on the above insight, quinoline derivatives were developed by condensing 2-aminoarylketones with carbonyl compounds owning a reactive methylene group, followed by cyclodehydration. Quantum chemical calculations were conducted at the B3LYP/6-311G­(d,p), CAM-B3LYP/6-311G­(d,p), and M06-2X/6-311G­(d,p) levels of theory in the gas phase to optimize the structure, determine vibrational frequencies, chemical shift values using NMR analysis, Hirshfeld surface analysis, highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO), molecular electrostatic potential (MEP) maps, nonlinear optical (NLO) properties, and thermodynamic properties. − Here, we would like to report a convenient and straightforward workup method for the synthesis of quinoline molecule ( 3 ) using freshly prepared polyphosphoric acid (PPA) − (P 2 O 5 in H 3 PO 4 ) under solvent-free conditions from 2-aminobenzophenone ( 1 ) and pentan-2,3-dione ( 2 ) through Friedländer quinoline synthesis.…”

Rhodium-catalyzed coupling-cyclization ofo-alkynyl/propargyl arylazides oro-azidoaryl acetylenic ketones with arylisocyanides: synthesis of 6H-indolo[2,3-b]quinolines, dibenzonaphthyridones and dihydrodibenzo[b,g] [1,8]-naphthyridines

“…3 Consequently, various methods based on different cyclization strategies have been developed to access these valuable fused tetracyclic heterocycles. In this field, transition metal-catalyzed cyclization strategies have become one of the most efficient methods for the synthesis of indolo[2,3- b ]quinoline 4 and dibenzonaphthyridine 5 derivatives. However, most of the reactions rely on the use of fused ring precursors as the coupling partners.…”