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Beilstein J. Org. Chem. 2014, 10, 1896–1905, doi:10.3762/bjoc.10.197
Graphical Abstract
Scheme 1: Mechanistic scheme of the formation of 2H-1,3-oxazine by the reaction of isoxazoles with a diazo co...
Scheme 2: Mechanistic scheme of the formation of 2H-1,3-oxazine by the reaction of azirine with a diazo compo...
Figure 1: Energy profiles for the transformations of ylides C, (3Z)-1-oxa-5-azahexa-1,3,5-triene D and oxazin...
Figure 2: Energy profiles for the transformations of (3Z)-1-oxa-5-azahexa-1,3,5-triene D and oxazines E deriv...
Scheme 3: Reaction of isoxazole 1a and diazo ester 2a.
Figure 3: Molecular structures of compounds 3a,k, displacement parameters are drawn at 50% probability level.
Figure 4: Molecular structures of compounds 4a,b, displacement parameters are drawn at 50% probability level.
Scheme 4: Isodesmic reactions for 1,3-oxazines 3d,e,n,o and 1-oxa-5-azahexa-1,3,5-trienes 4a,b,g,h.
Scheme 5: Reaction of complementary isoxazole 1a and azirine 5 with diazo esters.
Beilstein J. Org. Chem. 2014, 10, 784–793, doi:10.3762/bjoc.10.74
Scheme 1: Reactions of furan-2,3-diones 1 and azirines 2.
Figure 1: Molecular structures of compounds 3а, 4b.
Scheme 2: The route of formation of compounds 3 and possible intermediates in route to compounds 4 and 5.
Figure 2: Energy profiles for the reactions of azirines 2a,c and acylketene 6a, as well as acylketene 6a with...
Scheme 3: Possible intermediates in routes to compounds 4 and 5.
Figure 3: Energy profiles for the reactions of dihydropyrazine 11a with acylketene 6a, as well as acylketene ...
Figure 4: Energy profiles for the reactions of azirines 2a,c with protonated azirines 14a,c. Relative free en...
Scheme 4: Isodesmic equation for evaluation of relative basicity of azirines 2c,a.
Scheme 5: Reaction of furandione 1a with azirine 2d.
Figure 5: Molecular structure of compound 17.
Scheme 6: Reaction of furandione 1d with azirine 2a.
Scheme 7: Reactions of compounds 3d and 18a with methanol.