Reaction of 5,5-diphenyl-2-thiohydantoin with 1,3-dibromopropane : Crystal and molecular structure of 2,3,4,5-tetrahydro-6,6-diphenylimidazo [2, 1-b]-thiazine-7 (6H)-one

The reaction between the potassium salt of 5,5-diphenyl-2-thiohydantoin (1) and 1,3-dibromopropane carried out in DME under anhydrous conditions has been found to give two isomeric diphenylimidazothiazines 2 and 3. When the reaction of 1 with 1,3-dibromopropane was performed in protic solvents (EtOH, HOH, NaOH) 2 and 3-(3-mercaptopropyl) - 5,5 - diphenylthiohydantoin (4) were formed. The latter is the product of hydrolysis of 3 taking place under the reaction conditions. 2,3,4,5 - Tetrahydro - 6,6 - diphenylimidazo 2,1-b] - thiazine - 7 (6H) - one (2) crystallises in space group P2₁/n with a =10.812(3), b =14.905(7), c =9.885(4) Å, β = 104.91(2)°. The 5-membered ring in 2 is planar whereas the 6-membered thiazine ring adopts the sofa conformation.