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Efficient and Expeditious Synthesis of Pyrano‐pyrimidines, Multi‐substituted γ‐Pyrans, and Their Antioxidant Activity
Author(s) -
ElBayouki Khairy A. M.,
Basyouni Wahid M.,
Khatab Tamer K.,
ElBasyoni Fakhry A.,
Hamed Ahmed R.,
Mostafa Eslam A.
Publication year - 2014
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.2019
Subject(s) - chemistry , malononitrile , ethyl acetoacetate , acetic anhydride , yield (engineering) , catalysis , organic chemistry , acetic acid , solvent , antioxidant , sulfuric acid , pyran , materials science , metallurgy
An efficient, expeditious catalytic route for the synthesis of ethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐aryl‐4 H ‐pyran‐3‐carboxylates 2 was achieved via a three‐component, one‐pot reaction of malononitrile, ethyl acetoacetate, and various aromatic aldehydes in water as a solvent at room temperature. The key advantages are excellent yield, reaction time, and inexpensive catalyst. Also, cyclization of 4 H ‐pyrans 2 to the corresponding 4 H ‐pyrano[2,3‐ d ]pyrimidines 3 using silica sulfuric acid in the presence of acetic anhydride was described. Some synthesized compounds exhibited promising antioxidant activities.