Triphenyl verdazyl radicals' reactivity with alkyne carboxylates as a synthetic route to 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylates
A series of 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylates are synthesized by a unique reaction of triphenyl verdazyl radical with di-substituted electron deficient alkyne carboxylates. This transformation allows for the quick synthesis of this class of compounds in just three steps starting from a hydrazone. A radical mechanism that is consistent for the substitution patterns observed in the series of compounds made is proposed. The final product is obtained by a subsequent retro-Diels-Alder reaction.
Bancerz, Matthew,Prack, Ernest,Georges, Michael K.
supporting information; experimental part
p. 4026 - 4029
(2012/08/13)
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