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

• Authors: Oana Moldovan , Pedro Lameiras , Eric Henon , Flavia Popa , Agathe Martinez , Dominique Harakat , Carmen Sacalis , Yvan Ramondenc , Mircea Darabantu
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

Amino-s-triazines; NMR; Restricted rotation; Serinols

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 4
• Pages: 1119-1136

Dates

published

1 - 8 - 2012

online

29 - 5 - 2012

Contributors

author

Oana Moldovan

author

Pedro Lameiras

• ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France

author

Eric Henon

• ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France

author

Flavia Popa

author

Agathe Martinez

• ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France

author

Dominique Harakat

• ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France

author

Carmen Sacalis

• Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania

author

Yvan Ramondenc

• IRCOF — LCOFH, UMR 6014 CNRS COBRA, University and INSA of Rouen, 76821, Mont Saint-Aignan Cedex, France

author

Mircea Darabantu

• Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania

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Identifiers

DOI

10.2478/s11532-012-0015-4