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( E )‐2‐(4‐Arylbut‐1‐en‐3‐yn‐1‐yl)chromones as Synthons for the Synthesis of Xanthone‐1,2,3‐triazole Dyads
Author(s) -
Albuquerque Hélio M. T.,
Santos Clementina M. M.,
Cavaleiro José A. S.,
Silva Artur M. S.
Publication year - 2015
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.201500448
Subject(s) - chemistry , xanthone , cycloaddition , moiety , sodium azide , triazole , synthon , medicinal chemistry , ring (chemistry) , azide , click chemistry , aldol reaction , stereochemistry , organic chemistry , catalysis
Xanthone‐1,2,3‐triazole dyads have been synthesized by two different approaches, both starting from novel ( E )‐2‐(4‐arylbut‐1‐en‐3‐yn‐1‐yl)chromones, prepared through a base‐catalyzed aldol reaction of 2‐methylchromone and arylpropargyl aldehydes. In the first method, the xanthone moiety is built by Diels–Alder reaction of the referred unsaturated chromones with N ‐methylmaleimide under microwave irradiation, followed by oxidation of the obtained adducts with DDQ, whereas the 1,2,3‐triazole ring results from the cycloaddition reaction of the acetylene moiety with sodium azide. The second strategy first involves the cycloaddition reaction with sodium azide to provide the 1,2,3‐triazole ring, followed by methylation of the triazole NH group prior to Diels–Alder reaction with N ‐methylmaleimide. The last step in this synthesis of novel xanthone‐1,2,3‐triazole dyads entails oxidation of the cycloadducts with DDQ.