Metal-Assisted Ring-Closing/Opening Process of a Chiral Tetrahydroquinazoline
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https://figshare.com/articles/dataset/Metal_Assisted_Ring_Closing_Opening_Process_of_a_Chiral_Tetrahydroquinazoline/2552983
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资源简介：
The ring–chain tautomerism of a 2-aryl-1,2,3,4-tetrahydroquinazoline
has been exploited to induce reversible changes in the aminal–imine
equilibrium, as desired, by coordination of a suitable metal ion.
This process was studied by NMR and UV–vis spectroscopies,
X-ray crystallography, and molecular modeling approach. The results
obtained show that the imine H2Li undergoes
a selective ring-closing reaction upon complexation with Ni2+. As a result, complexes of the type Ni(HLa)2 are obtained, whose chirality arises from the chiral ligand H2La and the helicity of the structure. Hence, helical
enantiomers form the following racemates: [Δ-C(R,R)N(S,S),Λ-C(S,S)N(R,R)]-Ni(HLa)2·2HOAc and [Δ,Λ-C(S,R)N(R,S)]-Ni(HLa)2·4MeOH. In contrast to the
situation observed for Ni2+, the cyclic tautomer of the
ligand, H2La, undergoes a selective ring-opening
reaction upon complex formation with Pd2+, ultimately yielding
Pd(HLi)2·MeOH, in which the open-chain
imine ligand is bidentate through the N,O donor set of the quinoline residue. Density functional theory calculations
were conducted to provide insight into the different behavior of both
coordinated metals (Ni2+ and Pd2+) and to propose
a mechanism for the metal-assisted opening/closing reaction of the
tetrahydroquinazoline ring.
创建时间：
2016-02-22
