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).
Department of Chemistry, Loyola University Chicago, 1032 West Sheridan Road, Chicago, Illinois 60660, United States.
Andria M
AM
Panagopoulos
Matthias
M
Zeller
Daniel P
DP
Becker
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