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Synthesis of 6-Substituted 6-Nitroperhydro-1,4-diazepines via Novel Tandem Retro-Henry and Mannich/Michael Reactions

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journal contribution
posted on 22.02.2016, 07:01 by Jonathan Martinelli, Giuseppe Gugliotta, Lorenzo Tei
N,N′-Dibenzyl-6-hydroxymethyl-6-nitroperhydro-1,4-diazepine was converted into a nitronate via retro-Henry reaction, followed by either Michael reaction with several acrylic derivatives or Mannich reaction with different amines, thus leading to 6-substituted 6-nitroperhydro-1,4-diazepines. The tandem retro-Henry/Mannich reaction was also carried out using benzylamine as base, solvent, and reagent at the same time. Selective hydrogenation of the nitro group and complete hydrogenolysis were also successfully achieved.

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