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 C 2-symmetric saddle...

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Veröffentlicht in:	Journal of organic chemistry 2010-11, Vol.75 (22), p.7887-7892
Hauptverfasser:	Panagopoulos, Andria M, Zeller, Matthias, Becker, Daniel P
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Aza Compounds - chemical synthesis Aza Compounds - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Molecular Conformation Molecular Structure Organic chemistry Palladium - chemistry Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry Preparations and properties
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Zusammenfassung:	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 C 2-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo1017074