A new domino reaction based on [4+2]-cycloadditions of pyrido[1,2-a]pyrazines with azadienophiles

Citation
T. Billert et al., A new domino reaction based on [4+2]-cycloadditions of pyrido[1,2-a]pyrazines with azadienophiles, J HETERO CH, 36(3), 1999, pp. 627-633
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
36
Issue
3
Year of publication
1999
Pages
627 - 633
Database
ISI
SICI code
0022-152X(199905/06)36:3<627:ANDRBO>2.0.ZU;2-N
Abstract
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 involve s 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-phenyltriazolindi one 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 ox ygen gave oxadiazinones 8.