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Paper | Regular issue | Vol 83, No. 2, 2011, pp.323-330
Published online, 17th December, 2010
DOI: 10.3987/COM-10-12102
Efficient Synthesis of Functionalized Diazacyclopenta[c]pentalene with Multiple Intermolecular Interactions in Crystal

Konstantin V. Kudryavtsev*

*Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991, Moscow, Russia

Abstract

Atom economic synthesis of functionalized polysubstituted racemic diazacyclopenta[c]pentalene 7 has been developed using sequential organocatalytic 1,3-dipolar cycloaddition of azomethine ylide with maleic anhydride and three successive amide bonds formation induced by interaction of 4-fluorobenzylamine with heterocyclic anhydride 5. Enantiomers of 7 are connected by Cl-π, H···F and C=O···H intermolecular interactions in crystal.