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Structures and fluorescence of secondary products produced from the cope‐knoevenagel reaction of 2‐phenylpropionaldehyde with methyl cyanoacetate
Author(s) -
Nagai Wakatu,
Hirata Yumiko,
Kawai Masao,
Tanaka Kiyoaki
Publication year - 1996
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.5570330122
Subject(s) - chemistry , knoevenagel condensation , fluorescence , pyridine , ethyl cyanoacetate , organic chemistry , medicinal chemistry , malononitrile , catalysis , physics , quantum mechanics
The Cope‐Knoevenagel reaction of 2‐phenylpropionaldehyde ( 7 ) with methyl cyanoacetate ( 8 ) produced methyl ( E )‐2‐cyano‐4‐phenylpent‐2‐enoate ( 9 ) and the two highly fluorescent secondary products, 2‐amino‐3‐carbomethoxy‐6‐phenyl‐4‐(1‐phenylethyl)pyridine ( 10 ) and 3‐cyano‐6‐phenyl‐4‐(1‐phenylethyl)‐2‐pyridone ( 11 ). The structure of 10 was determined by X‐ray crystallography while the structure of 11 was confirmed by the conversion of 9 into 11 . The mechanism of their formation is discussed. Fluorescence of 10 and 11 and the related compounds are also described.