Conjugate addition of nitroalkanes to N-substituted maleimides. Synthesis of 3-alkylsuccinimides and pyrrolidines
3-Alkylidenesuccinimides obtained by conjugate addition of nitroalkanes to N-substituted maleimides can be reduced to the corresponding 3-alkyl derivatives by catalytic hydrogenation. 3-Alkylsuccinimides can be further reduced using BH3·Me
Nitroalkanes as alkyl anion synthons - A new approach to the synthesis of 2-substituted N-ethyl succinimides and 2-substituted succinate diesters via nitroalkanes
2-Substituted N-ethyl succinimide and 2-substituted succinate diesters were obtained by two key steps: (i) Michael addition of a nitroalkane to the appropriate enedione derivative under basic conditions (DBU), with the concomitant elimination of nitrous acid, and (ii) selective reduction of the obtained enone with nickel boride, in methanol/THF. In this context the nitroalkane acts as an alkyl anion synthon. By this method trimethyl tricarboxylates were also synthesized. VCH Verlagsgesellschaft mbH, 1996.
Ballini, Roberto,Bosica, Giovanna
p. 2087 - 2089
(2007/10/03)
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