62216-62-0Relevant academic research and scientific papers
Synthesis, reactions, and rearrangements of 2,4-diazabicyclo[3.1.0]hexan-3- ones
Helmut, C.,Stawitz, Josef Walter,Mueller, Bodo
, p. 2449 - 2463,15 (2020/08/24)
Copper-mediated cyclopropanation of 1,3-dialkyl-1,3- dihydroimidazol-2-ones with diazomethane and methyl diazoacetate yields 2,4-diazabicyclo[3.1.0]hexan- 3-ones and the first diaza[4.3.1]propellane. The bicyclic system survives elevated temperatures and in strongly basic and acidic solutions, but drastic conditions cleave the (C-1)-(C-6) bond affording 1,3-dihydroimidazol-2-ones. Catalytic hydrogenation removes N-benzyl groups and opens the (C-1)-(C-6) bond. Lithium aluminium hydride reduces 2,4-dibenzyl-2,4-diazabicyclo[3.1.0]hexan-3- one to a bicyclic aminal. Acid-induced cleavage of its imidazolidine ring is followed by unexpected transformations that probably procede via an acyclic intermediate, which comprises an azomethine ylide and an iminium moiety. 1,3-Cyclization involving both functional groups leads to N,N'-dibenzyl-trans-1, 2-cyclopropanediamine, while 1,5-cyclization gives rise to the formation of N-benzylpyrrole along with N-benzylamine.
