Research Article: Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate

Date Published: May 01, 2011

Publisher: International Union of Crystallography

Author(s): Liping Meng, James C. Fettinger, Mark J. Kurth.


The title mol­ecule, C22H23N3O2, was obtained via an intra­molecular cyclo­addition of an azomethine ylide and an alkene tethered by a benzimidazole unit. The benzoimidazole unit is essentially planar, with an r.m.s. deviation of 0.0087 Å from the nine constituent atoms. It has a cis fusion of the two pyrrolidine rings as well as a cis ester appendage. The two pyrrolidine rings rings have envelope conformations. The crystal packing is stabilized by aromatic π–π stacking of parallel benzimidazole ring systems, with a centroid-to-centroid distance of 3.518 (6) Å. Weak inter­molecular C—H⋯O contacts may also play a role in the stability of the packing.

Partial Text

Polycyclic nitro­gen-containing heterocycles form the basic skeleton of numerous alkaloids and physiologically active compounds, see: Southon & Buckingham (1989 ▶). Conformational studies have been reported for related pyrrolidino[3,4-b]pyrrolidine-2-carboxyl­ates obtained from intra­molecular cyclo­addition of azomethine ylides, see: Cheng et al. (2001 ▶); Meng et al. (2007 ▶). For related literature on the pharmaceutical properties of benzimidazole and pyrrolidine, see: Gudmundsson et al. (2000 ▶); Hamilton & Steiner (1997 ▶). For related literature on the azomethine ylide cycloaddition in similar systems, Pedrosa et al. (2006 ▶); Yang et al. (2006 ▶).




0 0 vote
Article Rating
Notify of
Inline Feedbacks
View all comments