Synthesis of an ortho-triazacyclophane: N,N',N''-trimethyltribenzo-1,4,7-triazacyclononatriene.
N,N',N''-trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the new cyclophane to have a C2-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).
Panagopoulos
Andria M
AM
Department of Chemistry, Loyola University Chicago, 1032 West Sheridan Road, Chicago, Illinois 60660, United States.
Zeller
Matthias
M
Becker
Daniel P
DP
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001372:Aza Compounds; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring; C000589592:N,N',N'-trimethyltribenzo-1,4,7-triazacyclononatriene; D011083:Polycyclic Compounds; C483859:cyclotriveratrylene; C539946:triazacyclophane; D010165:Palladium