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Heterotricyclic systems. Part I . Synthesis of new dipyridopyrazines
Author(s) -
Savelli Francesco,
Boido Alessandro
Publication year - 1992
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.5570290241
Subject(s) - chemistry , pyrazine , dehydrogenation , piperidine , pyridine , ring (chemistry) , tricyclic , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
Abstract Pursuing our previous research on azaquinoxalinones (1,2‐dihydropyrido[2,3‐ b ]/[3,4‐ b ]pyrazinones) we prepared, through a reductive cyclization of N ‐(3′‐nitropyridin‐2′‐yl)piperidine‐2‐carboxylic acids 3a‐c , a set of derivatives of a new tricyclic structure, 7,8,9,10‐tetrahydro‐5 H ‐dipyrido[1,2‐ a :3′,2′‐e]pyrazin‐6(6a H )‐ones 4a‐c. Starting from these compounds we obtained substituted amides 5a‐c and, from 4a , the amidines 6a‐c. In the synthesis of 6 , a dehydrogenation reaction occurred giving rise to 7. The compounds 9 and 10 , characterized by a different ring‐fusion between the pyridine and pyrazine rings, were synthesized in a similar manner.