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Sodium‐Hydroxide‐Mediated Synthesis of Highly Functionalized [1,6]‐Naphthyridines in a One‐Pot Pseudo Five‐Component Reaction
Author(s) -
Sarkar Satavisha,
Das Deb K.,
Khan Abu T.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300894
Subject(s) - malononitrile , chemistry , sodium hydroxide , aryl , organic chemistry , base (topology) , alkyl , alkoxy group , ethanol , medicinal chemistry , catalysis , mathematical analysis , mathematics
The synthesis of hitherto unreported 5‐amino‐7‐alkoxy‐2‐methyl‐2,4‐aryl‐1,2‐dihydro‐1,6‐naphthyridine‐8‐carbonitriles ( 4 ) was accomplished by a one‐pot pseudo five‐component reaction using aryl methyl ketones or alkyl methyl ketones, malononitrile, and alcohols in the presence of sodium hydroxide under reflux conditions. By following an identical reaction procedure, various 5‐amino‐2‐methyl‐2,4‐diaryl‐7‐(arylthio)‐1,2‐dihydro‐1,6‐naphthyridine‐8‐carbonitrile derivatives ( 6 ) were also synthesized from aryl methyl ketones, malononitrile, and thiophenols in the presence of sodium hydroxide in ethanol. High bond‐forming efficiency, good yields, and the use of a readily available base are some of the salient features of this multicomponent reaction.