Reaction of β-Nitroketeneaminal with Olefins Bearing Electron-Withdrawing Group and Aldehydes

Article abstract of DOI:10.1246/bcsj.63.1921

The reaction of 2-(nitromethylene)imidazolidine (1) with olefins bearing an electron-withdrawing group gave Michael-type addition products and/or 5-nitro-1,7-diazabicyclo<4.3.0>nonane derivatives derived from the Michael-type adduct.The reaction of 1 with α,β-unsaturated aldehydes in the presence of an acid, on the other hand, gave similar diazabicyclic derivatives and 2-<(2-imidazolidinylidene)nitromethylene>-5-nitro-1,7-diazabicyclo<4.3.0>non-5-ene derivatives.The reaction of 1 with saturated and aromatic aldehydes in the presence of hydrochloric acid gave 1,3-bis(2-imidazolidinylidene)-1,3-dinitropropane derivatives.The enhanced enaminic character of 1 is ascribable to the two electron-donating amino groups fixed in a five-membered ring.