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A new domino reaction based on [4+2]‐cycloadditions of pyrido[1,2‐ a ]pyrazines with azadienophiles
Author(s) -
Billert Thomas,
Beckert Rainer,
Brandenburg Jörg,
Fehling Peer,
Döring Manfred,
Görls Helmar,
Langer Peter
Publication year - 1999
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.5570360309
Subject(s) - chemistry , regioselectivity , cycloaddition , domino , ring (chemistry) , reaction conditions , cascade reaction , nitroso , nitroso compounds , medicinal chemistry , triazine , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
The reaction of pyrido[1,2‐ a ]pyrazines 1 with nitroso compounds 2 provides pyridyl substituted 1,2,4‐triazinones 4 via a domino reaction which involves a cycloaddition and a ring transformation reaction. The intermediate and regioselective formed oxadiazines 4′ were trapped by complexation yielding the (CO) 4 Mo‐complex 5. Derivatives of diazene such as N ‐phenyltriazolindione 6a , phthalazinedione 6b or esters of azodicarboxylic acid 6c‐6f reacted with 1 to give different derivatives of 1,2,4‐triazine 7a‐f . The use of oxygen gave oxadiazinones 8 .