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Paper | Regular issue | Vol 85, No. 10, 2012, pp.2449-2463
Published online, 14th August, 2012
DOI: 10.3987/COM-12-12543
Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones

Helmut Quast,* Josef Walter Stawitz, and Bodo Mueller

*Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany

Abstract

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-benzylpyrrol along with N-benzylamine.