Modular Synthesis of Helicene‐Like Compounds Based on the Imidazolium Motif1. Issue 26 (7th August 2014)

• Record Type: Journal Article
• Authors: Čížková, Martina; Šaman, David; Koval, Dušan; Kašička, Václav; Klepetářová, Blanka; Císařová, Ivana; Teplý, Filip
• Is Part Of: European journal of organic chemistry. Issue 26(2014)
• Page Start: 5681
• Page End: 5685
• Publication Date: 2014-08-07
• Subjects: Synthetic methods -- Nitrogen heterocycles -- Helical structures -- [2+2+2] Cycloaddition -- Electrophoresis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402746
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Straightforward synthesis of novel mono‐ and tricationic helical compounds based on the imidazolium core has been developed. The synthetic route based on double [2+2+2] cycloaddition reactions of precursors with the imidazolium core motif is notably modular and reaches beyond established protocols used for the synthesis of imidazolium systems as well as beyond the reported protocols used to assemble compounds with helical frameworks. This approach opens rapid four‐step access to a cationic species featuring nine ortho ‐annulated rings that represents the highest order helical nitrogen‐based cationic system reported to date. Abstract : Straightforward assembly of helicene‐like cationic systems based on the imidazolium core is introduced. The strategy takes advantage of double [2+2+2] cycloaddition reactions and opens rapid four‐step access to a cationic helical species featuring nine ortho ‐annulated rings.