S. V. Shorunov, M. B. Plutschack, M. V. Bermeshev, I. A. Guzei, “Synthesis and unusual photochemistry of a highly reactive pyrimidinedione”, Mendeleev Commun., 2018, Volume 28, Issue 5,Pages <nobr>501

Communications

Synthesis and unusual photochemistry of a highly reactive pyrimidinedione

S. V. Shorunov^a, M. B. Plutschack^b, M. V. Bermeshev^a, I. A. Guzei^b

^a A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation
^b Department of Chemistry, University of Wisconsin, Madison, USA

Abstract: The herein obtained 3-methyl-5,5-diphenylpyrimidine-2,4-(3H,5H)-dione forms upon photolysis an unusual bicyclic product, namely, 6-methyl-3,3,8,8-tetraphenyl-8,8a-dihydroimidazo[1.5-c]pyrimidine-5,7(3H,6H)-dione in 21% yield. The transformation starts with elimination of carbon monoxide and methyl isocyanate from the molecule of substrate via a ‘Type A’ photochemical process giving 3,3-diphenylazirine. Then 1,3-dipole species generated from the latter is trapped by the starting compound via a [3+2] cycloaddition.

Language: English

DOI: 10.1016/j.mencom.2018.09.016

	*Supplementary materials:*
		Supplementary_data_1.pdf	221.2 Kb