Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 784-793Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.74
Keywords
acylketene; azirine; domino reaction; furandione
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Funding
- Russian Foundation for Basic Research [14-03-00187]
- Saint Petersburg State University [12.38.78.2012]
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3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1] undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a, 12,12a-tetrahydrobis[1,3] oxazino[3,2-a:3',2'-d]pyrazine-4,10diones. The latter compounds, with a new heterocyclic skeleton, are the result of the coupling of two molecules of azirine and two molecules of acylketene and can be prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3] oxazino[3,2-a: 3', 2'-d] pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition of the latter to two molecules of acylketenes.
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