Novel regioselective hydroxyl-alkylation of 4,5-diphenylimidazole-2-thione and a competitive intramolecular ring closure of the S-hydroxyalkyl-imidazoles to imidazo[2,1-b]thiazines and thiazoles. Role of catalyst, microwave irradiation, and solid support.
Under both conventional method (CM) and microwave (MW) irradiation (MWI) conditions, alkylation of 4,5-diphenylimidazole-2-thione (1) with halogeno-alkanols 2 or 5, chloroglycerol 11 and 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (8) in presence of sodium ethoxide or sodium acetate in alcohol afforded regioselectively the corresponding S-alkylated analogues 3, 6, 9, and 12; they also were obtained using MW in absence and presence of bentonite as solid support with no change in regioselectivity. In the presence of potassium carbonate in DMF, the bisalkylated analogues 4, 7, 10, and 13 were obtained except in case of compound 13 where it was accompanied with the imidazothiazine 14. A convenient approach for imidazo-[2,1-b]thiazines and thiazoles 14-16 could be achieved by intramolecular dehydrative ring closure of the S-hydroxyalkylated imidazoles 3, 6, and 12 using potassium carbonate in DMF under both conventional and microwave methods. Isopropylidenation of 12 and 13 and deprotection of 9 and 10 also were investigated.
Ashry
E S H El
ES
Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt. eelashry@hotmail.com
Rashed
N
N
Awad
L F
LF
Ramadan
E
E
Abdel-Maggeed
S M
SM
Rezki
N
N
D000478:Alkylation / Q000528:radiation effects; D002384:Catalysis / Q000528:radiation effects; D005990:Glycerol / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013843:Thiazines / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013871:Thiones / Q000737:chemistry*
D007093:Imidazoles; D009705:Nucleosides; D012997:Solvents; D013843:Thiazines; D013844:Thiazoles; D013871:Thiones; D005990:Glycerol