Reactions of phosphorus trihalides with 6-(adamantan-1-yl)imidazo[2,1-b]thiazoles

Abstract

We found that 6-(adamantan-1-yl)imidazothiazoles Ia–Ic do not react with phosphorus trichloride under similar conditions. (Adamantan-1-yl)imidazothiazole Ia reacts with phosphorus tribromide to yield the compound IIa, whereas the reactions of adamantlyimidazothiazoles Ib and Ic give rise to the dibromoderivatives IIIa and IIIb. Compounds Ia–Ic give the analogous products at reflux in liquid bromine. Compounds IIa–IIc were formed under milder conditions [3] in the reaction of equimolar amounts of the studied thiazoles with bromine in chloroform. zolium bromide IVa. Yield 93%, mp 128–130°C. H NMR spectrum, δ, ppm: 1.73 s (6H, 4',6',10'-CH2), 1.87 s (6H, 2',8',9'-CH2), 2.01 s (3H, 3',5',7'-CH), 2.34 s (3H, Me), 6.74 s (1H, 5-H), 7.37 s (1H, 3-H). Found N, %: 10.20. C16H20N2S. Calculated N, %: 10.28.