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Intramolecularly hydrogen‐bonded 3‐phenacyl‐l H ‐pyrido[3,4‐ b ]‐pyrazin‐2‐one and 2‐Phenacyl‐4 H ‐pyrido[3,4‐ b ]pyrazin‐3‐one
Author(s) -
Seki Taketsugu,
Iwanami Yasuo
Publication year - 1994
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.5570310462
Subject(s) - phenacyl , chemistry , hydrogen bond , ring (chemistry) , side chain , stereochemistry , chelation , crystallography , nitrogen atom , proton nmr , medicinal chemistry , molecule , organic chemistry , polymer
Twelve phenacyl derivatives of 1 H ‐pyrido[3,4‐ b ]pyrazin‐2‐ones and 4 H ‐pyrido[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 and those at the 1 and 2 positions in the latter compounds migrate onto the side chains to form phenacyli‐dene structures. These migrations are facilitated by chelation between side chain carbonyl and the proton attached to the ring nitrogen atom which was generated by the migration. All the hydrogen‐bonded structures appear to be stable as shown by their ir spectra in the crystalline state, and by their 1 H nmr spectra in solution.