New bis-oxalamides from trans-1,2-diaminocyclohexane

Abstract

The synthesis of six new bis-oxalamides 2-7 derived from trans-1,2-diaminocyclohexane and aliphatic amines is reported. These compounds were characterized by IR, MS and 1 H and 13 C NMR spectroscopy.

Intramolecular hydrogen bond directed stable conformations of benzoyl phenyl oxalamides: unambiguous evidence from extensive NMR studies and DFT-based computations

“…As a result these molecules may become involved in both intra- and inter-molecular HBs. 35 The intramolecular HB dictates the geometry and conformation of oxalamides, and at the same time the stability can be examined through the intermolecular HB. 36–38 The presence of such weak molecular interactions in oxalamide structures leads to a diverse range of applications, viz.…”

Positional Isomerism and Steric Effects in the Self-Assemblies of Phenylene Bis-Monothiooxalamides

“…The intramolecular hydrogen bonding scheme in compounds 1−9 is like that exhibited by analogous phenylene bisoxalamides, characterized by the juxtaposition of a series of [S(5)], [S(6)], and [S (7)] rings. They are formed by 3 )] 2 interactions.…”

“…Oxalamide derivatives are flat due to the formation of intramolecular hydrogen bonds between the acidic protons of amides and the carbonyl oxygen atoms of these fragments. − Thiooxalamides and oxalamides are isostructural analogues; they differ in size and polarity due to the exchange of oxygen by sulfur in one or both carbonyls. Thiooxalamides, such as oxalamides, adopt the trans disposition between the amide proton and thiocarbonyl moieties which is stabilized by the formation of intramolecular NH···SC hydrogen bonding interactions .…”

Modular Chiral Bisoxalamide–Copper-Catalyzed Asymmetric Oxo-Diels–Alder Reaction: Carbonyl Coordination for High Enantio- and Diastereocontrols

“…Traditionally, chiral bisoxazolines, N , N ′-dioxides, and phosphoric acid have been used in combination with some transition or main group metals for effective catalysis of this asymmetric transformation . We envisioned that chiral bis-oxalamides, in spite of the relatively weak ligating power of the carbonyl group with Lewis acidic metals, would be an appealing target for the development of chiral ligands. In comparison with the well-established privileged C 2 -symmetric bis­(oxazoline) ligands, the new CBOA ligands should also be easily amenable to fine tuning of the stereoelectronic properties owing to their modular nature, with further advantages of ready synthesis and robust oxalic diamide bonds as an extra bonus, which are valuable features for practical applications wherein the scalable, cost-effective, and efficient ligand preparation is of major concern.…”