INTRAMOLECULARLY HYDROGEN-BONDED 3-PHENACYL-1H-PYRIDO[3,4-B]-PYRAZIN-2-ONE AND 2-PHENACYL-4H-PYRIDO[3,4-B]PYRAZIN-3-ONE

Authors
Citation
T. Seki et Y. Iwanami, INTRAMOLECULARLY HYDROGEN-BONDED 3-PHENACYL-1H-PYRIDO[3,4-B]-PYRAZIN-2-ONE AND 2-PHENACYL-4H-PYRIDO[3,4-B]PYRAZIN-3-ONE, Journal of heterocyclic chemistry, 31(4), 1994, pp. 1065-1067
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022152X
Volume
31
Issue
4
Year of publication
1994
Pages
1065 - 1067
Database
ISI
SICI code
0022-152X(1994)31:4<1065:IH3>2.0.ZU;2-S
Abstract
Twelve phenacyl derivatives of 1H-pyrido[3,4-b]pyrazin-2-ones and 4H-p yrido[3,4-b]pyrazin-3-ones have been synthesized. In these compounds, C = N double bonds at the 3 and 4 positions in the former compounds an d those at the 1 and 2 positions in the latter compounds migrate onto the side chains to form phenacylidene structures. These migrations are facilitated by chelation between side chain carbonyl and the proton a ttached to the ring nitrogen atom which was generated by the migration . All the hydrogen-bonded structures appear to be stable as shown by t heir ir spectra in the crystalline state, and by their H-1 nmr spectra in solution.