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Flavonoids. 41 . Stereospecific synthesis of 2,3‐dihydro‐ c ‐3‐substituted‐ t ‐3‐methyl‐ r ‐2‐phenyl‐4 H ‐1‐benzopyran‐4‐ones
Author(s) -
Patonay Tamás,
PatonayPéli Erzsébet,
Litkei György,
Szilágyi László,
Batta Gyula,
Dinya Zoltán
Publication year - 1988
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.5570250158
Subject(s) - chemistry , stereospecificity , benzopyran , nucleophile , mesylate , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The synthesis of 2,3‐dihydro‐ t ‐3‐mesyloxy‐c‐3‐methyl‐ r ‐2‐phenyl‐4 H ‐1‐benzopyran‐4‐one (1) is described. The reaction of mesylate 1 with various nucleophiles, first of all O ‐ and N ‐nucleophiles, yields the corresponding 2,3‐dihydro‐ c ‐3‐substituted‐ t ‐3‐methyl‐ r ‐2‐phenyl‐4 H ‐1‐benzopyran‐4‐ones 2b, 7b, 9, 10, 12, 14 and 18 . Azide 14 is a useful intermediate for the synthesis of flavonoids 15–17 .