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New serinolic amino-s-triazines by chemoselective amination of cyanuric chloride and their (pro)diastereomerism in restricted rotational phenomena

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Moldovan O., Lameiras P., Henon E., Popa F., Martinez A., Harakat D., Sacalis C., Ramondenc Y., Darabantu M.

Open Chemistry

2012

vol. 10

issue 4

1119-1136

The highly chemoselective preparation of new elaborated N-unsymmetrically substituted chlorodiamino-s-triazines and melamines, seen as building-blocks for iterative synthesis, is reported. It consisted of amination of cyanuric chloride with commercial C-2-substituted 2-aminopropane-1,3-diols (“serinols”), playing the role as “open-chain” unit and enantiopure (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diols (“p-nitrophenylserinols”) based amino-1,3-dioxanes (“closed-chain” unit). Issued from the restricted rotation about C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, a global four-component rotational equilibrium involving the title compounds is discussed based on DFT computation and (VT) NMR data. Depending on π-deficiency of the s-triazine core, an (un)synchronised deblocking of the generated rotational diastereomers was observed. They are discussed as influence of intra-vs. intermolecular NH...OH (dynamic) interactions occurring in the “open-chain” unit and the anancomeric, axial vs. equatorial, amino-anchorage of the “closed-chain” unit. [...]

Synthesis and stereochemistry of some new 1,3,5-tris(1,3-dioxan-2-yl)-benzene derivatives

100%

Florian M., Cîrcu M., Toupet L., Terec A., Grosu I., Ramondenc Y., Dincă N., Plé G.

Open Chemistry

2006

vol. 4

issue 4

808-821

The synthesis and the stereochemistry of new 1,3,5-tris(1,3-dioxan-2-yl)-benzene derivatives are reported. The anancomeric structure and the axial orientation of the aryl group with respect to all 1,3-dioxane rings, and the cis-trans isomerism of some of the compounds are revealed. The data are supported by NMR investigations and by the molecular structure of one compound determined by single crystal X-ray diffractometry.

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2 Open Chemistry

1 2012

1 2006

2 Ramondenc Y.

1 Cîrcu M.

1 Darabantu M.

1 Dincă N.

1 Florian M.

1 Grosu I.

1 Harakat D.

1 Henon E.

1 Lameiras P.

1 Martinez A.

1 Moldovan O.

1 Plé G.

1 Popa F.

1 Sacalis C.

1 Terec A.

1 Toupet L.

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New serinolic amino-s-triazines by chemoselective amination of cyanuric chloride and their (pro)diastereomerism in restricted rotational phenomena

Synthesis and stereochemistry of some new 1,3,5-tris(1,3-dioxan-2-yl)-benzene derivatives