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

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‐cataly...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2021-09, Vol.58 (9), p.1809-1824
Main Authors: Kolandaivel, Prabha, Rajendran, Satheeshkumar, Karnam Jayarampillai, Rajendra Prasad
Format: Article
Language:English
Subjects:
Acetic acid
Amines
Aniline
Organic compounds
Quinoline
Substitutes
Synthesis
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Summary: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).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4312