Synthesis and Crystal Structure of a Novel Glycoluril Molecular Scaffold

• Published in: Journal of chemical crystallography 2016-04, Vol.46 (4), p.208-212
• Main Authors: Wang, Zhi-guo, Yu, Wei, Zheng, He-qi, Wang, Zhi-gang
• Format: Article
• Language: English
• Subjects: Brief Communication; Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Inorganic Chemistry; Organometallic Chemistry; Physical Chemistry
• ISSN: 1074-1542; 1572-8854
• DOI: 10.1007/s10870-016-0646-y

A novel glycoluril scaffold 1 , namely 1,6-(1,2-xylylene)-3,4-(1,3-dimetheneyl-hexahydropyrimidine)tetrahydroimidazo[4,5-d]imidazole-2,5(1 H ,3 H )-dione, was synthesized by the Mannich reaction of 1,6-(1,2-xylylene)tetrahydroimidazo[4,5- d ]imidazole-2,5(1 H ,3 H )-dione 5 with propanediamine and paraformaldehyde. The yielded product 1 was confirmed with IR, NMR, EI-MS. X-ray crystallographic technique was also conducted and the result showed the crystal belongs to monoclinic system, space group P2 1 /c with unit cell parameters a = 10.6892(11) Å, b = 12.1226(9) Å, c = 13.7822(13) Å, α = 90°, β = 112.620(4)°,γ = 90°, V = 1648.5(3) Å 3 , Z = 4, D c  = 1.428, M r  = 354.41, μ = 0.098 mm −1 , F(000) = 752, R 1  = 0.0522 and wR 2  = 0.1138. Graphical Abstract A novel molecular scaffold, containing a heterocyclic ring instead of an aromatic ring, was synthesized by the Mannich reaction based on glycoluril.