Abstract
Synthesis of highly substituted pyrazines from geminal diazides via thermal or copper-mediated cyclization and modification of the obtained pyrazines.
Highlights
The synthesis of pyrazines is described using a sequence that begins with the diazidation of N-allyl malonamides followed by thermal or copper-mediated cyclization
As part of our ongoing studies to unveil the reactivity of geminal diazido compounds,[13] we recently showed that 2,2diazido-3-oxohept-6-enoates gave 3-hydroxypyridines upon thermolysis (Scheme 1).[14]
The subsequent diazidation of the N-allyl malonamides 5 was achieved with iodine and sodium azide in aqueous DMSO at room temperature, a method we recently developed as a general entry toward diazides derived from 1,3-dicarbonyl compounds.[16]
Summary
The synthesis of pyrazines is described using a sequence that begins with the diazidation of N-allyl malonamides followed by thermal or copper-mediated cyclization. As part of our ongoing studies to unveil the reactivity of geminal diazido compounds,[13] we recently showed that 2,2diazido-3-oxohept-6-enoates gave 3-hydroxypyridines upon thermolysis (Scheme 1).[14] We questioned whether, starting with diazido compounds 1 derived from N-allyl malonamides, pyrazines 2 may become accessible in a fully analogous way. Earlier studies demonstrated how nitrogen-containing heterocycles can be synthesized from precursor compounds possessing the geminal diazido moiety.[15] To our knowledge, this is the rst study to successfully convert diazidated N-allyl malonamides into pyrazines through simple thermolysis.
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