3 years ago

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, Sandra Rubio, Solène Savrimoutou, François Hallé, Stéphane Moreau, Pascal Sonnet, Mathieu Marchivie

Publication date: November 2018

Source: Comptes Rendus Chimie, Volume 21, Issue 11

Author(s): Jean Guillon, Sandra Rubio, Solène Savrimoutou, François Hallé, Stéphane Moreau, Pascal Sonnet, Mathieu Marchivie

Abstract

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.

Resume

La structure complète de la 2-(4,5-dihydro-5-phénoxymethyl-1,3-oxazol-2-ylamino)-7-(2-hydroxy-3-phénoxypropyl)hexahydro-2H,6H-pyrimido[6,1-b][1,3]oxazin-6-one 1, une structure d'adduit formée lors de la réaction de la 5-(phénoxyméthyl)-2-amino-2-oxazoline et de l'acroléine, a été établie sans équivoque par une analyse cristallographique aux rayons X. Le présent travail porte sur l'identification structurale de l'adduit 1 et présente un mécanisme plausible pour sa formation. La molécule cristallise dans le système monoclinique, dans le groupe spatial P21/c avec 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 et wR = 0.1584.

Graphical abstract

Image 1

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