STRUCTURES AND FLUORESCENCE OF SECONDARY PRODUCTS PRODUCED FROM THE COPE-KNOEVENAGEL REACTION OF 2-PHENYLPROPIONALDEHYDE WITH METHYL CYANOACETATE

Authors
NAGAI W HIRATA Y KAWAI M TANAKA K
Citation
W. Nagai et al., STRUCTURES AND FLUORESCENCE OF SECONDARY PRODUCTS PRODUCED FROM THE COPE-KNOEVENAGEL REACTION OF 2-PHENYLPROPIONALDEHYDE WITH METHYL CYANOACETATE, Journal of heterocyclic chemistry, 33(1), 1996, pp. 123-128
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
33
Issue
1
Year of publication
1996
Pages
123 - 128
Database
ISI
SICI code
0022-152X(1996)33:1<123:SAFOSP>2.0.ZU;2-H
Abstract
The Cope-Knoevenagel reaction of 2-phenylpropionaldehyde (7) with meth yl cyanoacetate (8) produced methyl (E)-2-cyano-4-phenylpent-2-enoate (9) and the two highly fluorescent secondary products, -3-carbomethoxy -6-phenyl-4-(1-phenylethyl)pyridine (10) and 3-cyano-6-phenyl-4-(1-phe nylethyl)-2-pyridone (11). The structure of 10 was determined by X-ray crystallography while the structure of 11 was confirmed by the conver sion of 9 into 11. The mechanism of their formation is discussed. Fluo rescence of 10 and 11 and the related compounds are also described.