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Condensed heterocyclic lactams. I . Study on the cyclization methods resulting in 4‐aryl‐3,4‐dihydroquinolin‐2(1 H )‐ones
Author(s) -
Hazai László,
Deák Gyula,
Sohár Pál,
Tóth Gábor,
Tamás József
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280414
Subject(s) - chemistry , substituent , yield (engineering) , nitro , aryl , derivative (finance) , cinnamic acid , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl , materials science , economics , financial economics , metallurgy
Cyclization reactions with polyphosphoric acid of 3‐aryl‐3‐hydroxypropionanilides carrying a p ‐nitro‐ 7a or p ‐amino substituent 10 on the C‐3 phenyl group were investigated. In the case of p ‐nitro substitution the preferred reaction is, instead of cyclization, the elimination of water to give the corresponding cinnamic acid derivative. On the other hand, reaction of the p ‐amino‐substituted analogue gave the new compound 4‐(4‐aminophenyl)‐3,4‐dihydroquinolin‐2(1 H )‐one ( 2b ) in a good yield. The intermediate product of the cyclization was isolated and its structure established.