Synthesis of Helquats Based on Phenanthridinium Units: Four-Step Procedure to Novel Extended Helical Dications

Manoj R. Sonawane; Jan Vávra; David Šaman; Ivana Císařová; Filip Teplý

doi:10.1055/s-0034-1381136

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(22): 3479-3488
DOI: 10.1055/s-0034-1381136

paper

Synthesis of Helquats Based on Phenanthridinium Units: Four-Step Procedure to Novel Extended Helical Dications

Autor*innen

Manoj R. Sonawane

^aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo n. 2, 166 10 Prague 6, Czech Republic eMail: teply@uochb.cas.cz
Jan Vávra

^aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo n. 2, 166 10 Prague 6, Czech Republic eMail: teply@uochb.cas.cz
David Šaman

^aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo n. 2, 166 10 Prague 6, Czech Republic eMail: teply@uochb.cas.cz
Ivana Císařová

^bDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030/8, 128 43 Prague 2, Czech Republic
Filip Teplý*

^aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo n. 2, 166 10 Prague 6, Czech Republic eMail: teply@uochb.cas.cz

Abstract

Alle Artikel dieser Rubrik

Abstract

Three novel helical dications (helquats) containing phenanthridinium units have been synthesized from 6-(pyridin-2-ylethynyl)phenanthridine as a common precursor prepared by Sonogashira coupling of phenanthridin-6-yl triflate with 2-ethynylpyridine. Bisquaternization of the common precursor followed by rhodium-catalyzed [2+2+2] cycloisomerization led to the title helical dicationic scaffolds. The connectivity and spatial arrangement of the three target helquats were unambiguously established by X-ray crystal structure analysis.

Key words

helical structures - rhodium - catalysis - cycloadditions - heterocycles - Sonogashira coupling - helquats - heteroaromatic cations

Volltext

Referenzen

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Zusatzmaterial

Supporting Information (PDF) (opens in new window)