Crystal structure and identification of a pyrimido[6,1-b][1,3]oxazin-6-one derivative from the reaction of acrolein with 5-(phenoxymethyl)-2-amino-2-oxazoline

Jean Guillon (1) , Sandra Rubio (1) , Solène Savrimoutou (1) , François Hallé (1) , Stéphane Moreau (1) , Pascal Sonnet (2) , Mathieu Marchivie (3)

1 ARNA - Acides Nucléiques : Régulations Naturelle et Artificielle
2 AGIR - Agents infectieux, résistance et chimiothérapie - UR UPJV 4294
3 ICMCB - Institut de Chimie de la Matière Condensée de Bordeaux

The X-ray crystal structure of 2-(4,5-dihydro-5-phenoxymethyl-1,3-oxazol-2-ylamino)-7-(2-hydroxy-3-phenoxypropyl)hexahydro-2H,6H-pyrimido[6,1-b][1,3]oxazin-6-one (1), a structure of adduct formed by the reaction of 5-(phenoxymethyl)-2-amino-2-oxazoline and acrolein, has been established. The present work deals with the structural identification of the adduct 1 and presents a plausible mechanism for its formation. It crystallizes in the monoclinic space group P21/c with cell parameters a = 21.3337 (10) Å, b = 11.3712 (7) Å, c = 10.4936 (7) Å, β = 103.041 (3), V = 2480.0 (3) Å3, Z = 4. C26H32N4O6, Dc = 1.330 g/cm3, μ (Cu Kα) = 1.5418 Å, S = 1.188, F (000) = 1056, R = 0.0501, and wR = 0.1584.

Mots clés: Pyrimido[6; 1-b][1; 3]oxazin-6-one; 2-Amino-2-oxazoline; Michael reaction; X-ray crystal structure

Domaines: Matériaux

Jean Guillon, Sandra Rubio, Solène Savrimoutou, François Hallé, Stéphane Moreau, et al.. Crystal structure and identification of a pyrimido[6,1-b][1,3]oxazin-6-one derivative from the reaction of acrolein with 5-(phenoxymethyl)-2-amino-2-oxazoline. Comptes Rendus. Chimie, 2018, 21 (11), pp.987-992. ⟨10.1016/j.crci.2018.09.013⟩. ⟨hal-01922305⟩