Diversity-oriented synthesis of benzimidazole, benzoxazole, benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate-CuSO4-mediated oxidative coupling reactions of aldehydes in aqueous micelles.
Libraries of 2-substituted-benzimidazoles, benzoxazoles, benzothiazoles as well as quinazolin-4(3H)-ones were synthesized via potassium persulfate-CuSO(4)-mediated oxidative coupling of aldehydes with o-phenylenediamines, o-aminophenols, o-aminothiophenols, and anthranilamide, respectively, in aqueous micelles. The strategy opens a way for rapid generation of libraries of small heterocycles for biological screening. The reagent is commercially available, cheap, and highly chemoselective. The yields were superior in aqueous micelles to those in organic solvents. Short reaction times, large-scale synthesis, excellent chemoselectivity, excellent yields, as well as environmental friendliness are the main advantages of this diversity-oriented synthesis.
Kumar
Atul
A
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, 226001, India. dratulsax@gmail.com
Maurya
Ram Awatar
RA
Saxena
Deepti
D
D000447:Aldehydes / Q000737:chemistry*; D001562:Benzimidazoles / Q000138:chemical synthesis; D052160:Benzothiazoles / Q000138:chemical synthesis*; D001583:Benzoxazoles / Q000138:chemical synthesis; D019327:Copper Sulfate / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D008823:Micelles; D010084:Oxidation-Reduction; D017680:Potassium Compounds / Q000737:chemistry*; D052999:Quinazolinones / Q000138:chemical synthesis; D013431:Sulfates / Q000737:chemistry*
D000447:Aldehydes; D001562:Benzimidazoles; D052160:Benzothiazoles; D001583:Benzoxazoles; D006574:Heterocyclic Compounds, 2-Ring; D008823:Micelles; D017680:Potassium Compounds; D052999:Quinazolinones; D013431:Sulfates; C009007:potassium persulfate; D019327:Copper Sulfate