Strukturen von Chino[7,8‐h]chinolin und Chino[8,7‐h]chinolin

Abstract

Nahezu planar sind die beiden Titelverbindungen 1 und 2 im Kristall. Durch Röntgenstrukturanalyse beider Verbindungen konnten über Jahrzehnte bestehende Unsicherheiten bezüglich Synthese und Strukturzuordnung ausgeräumt werden. Bei der extrem starken und auch kinetisch aktiven Base 1 fällt der große zentrale äußere Winkel der Naphthalineinheit auf (125.4°), der einen relativ großen N ⃛N‐Abstand (272.8 pm) ermöglicht.

Transition Metal Complexes with the Proton Sponge 4,9-Dichloroquino[7,8-h]quinoline: Highly Twisted Aromatic Systems and an Extreme “Out-of-Plane” Position of the Coordinated Transition Metal Atom

“…[1] In previous syntheses access to the heterocyclic bithiazole core was based exclusively on the classical Hantzsch thiazole methodology. [2] Because of their regioselectivity [3] Pd-catalyzed cross-coupling reactions [4] of 2,4-dibromothiazole [5] appeared to offer an alternative shorter entry into bithiazoles which would allow a great variability in the choice of substituents at the 2'-and 4-positions. Herein we report the application of this strategy to the total synthesis of cystothiazole E (1).…”

The Proton Sponge Effect: Substitution of Quino[7,8‐h]quinoline and the First Structurally Characterised Derivatives

“…[3] During the intervening quarter century, very few research groups have explored the coordination ability of this intriguing ligand, with just a handful of reports on the subject to date. Substitutions at the 2, 11-, 4,9-and 6,7-positions of quino[7,8-h]quinoline were also successfully performed.…”

The first structurally characterised copper(II) complexes of quino[7,8-h]quinoline ligands

“…Intellectual protection of such ligands is on the increase too, due in part to increasing utility in fields as diverse as catalysis and modern electronics which exploit both strained structural motifs and unique photophysical behaviours [1][2][3][4]. Despite the successful synthesis of quino [7,8-h]quinoline being first reported 25 years ago [5,6], the metal coordination chemistry of the visually appealing ligand has received little attention, with just one report of successful transition metal coordination to date [7]. We believe that this was due to the difficulty of the ligand synthesis, but our recently reported milder synthetic route to these ligands now allows the full potential of this class of ligand to be explored [8].…”