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Reactions of 3‐Acylchromones with Heterocyclic Ketene Aminals: One‐Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives
Author(s) -
Savych Iryna,
Ejaz Syeda Abida,
Shah Syed Jawad Ali,
Iaroshenko Viktor O.,
Villinger Alexander,
Sosnovskikh Vyacheslav Ya.,
Iqbal Jamshed,
Abbasi Afshin,
Langer Peter
Publication year - 2017
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.201601138
Subject(s) - chemistry , moiety , ketene , chromone , pyridine , ring (chemistry) , stereochemistry , nucleophile , domino , pyrone , medicinal chemistry , organic chemistry , catalysis
Domino reactions of 3‐acylchromones, namely 3‐methoxalyl‐, 3‐aroyl‐ and 3‐cinnamoylchromones, with heterocyclic ketene aminals (HKAs) proceed by attack of the nucleophile on the C‐2 atom of the chromone moiety, pyrone ring‐opening and subsequent formal [3+3] cyclocondensation with formation of functionalized tetracyclic fused chromeno[2,3‐ b ]pyridines or 2 H ,3 H ‐imidazo[1,2‐ a ]pyridines. The product distribution depends on the type of acyl group located at the 3‐position of the chromone and on the size of the heterocyclic moiety of the HKAs. The products show considerable activity as selective phosphatase inhibitors.