Multidisciplinary synthetic approach for rapid combinatorial library synthesis of triaza-fluorenes.
A new multidisciplinary synthetic approach comprising polymer-support synthesis, microwave-assisted synthesis, and multicomponent condensation facilitates synthesis of triaza-fluorenes library with a set of advantages such as rapid process, simple purification, and structural diversity in one shot. Microwave-assisted multistep synthetic protocol was used to construct the benzimidazole ring on soluble polymer support using activated aryl-fluorides. The PEG anchored aryl fluoride was condensed with selective primary amines via an ipso-fluoro displacement reaction followed by reduction of nitro group. The subsequent cyclization with cyanogen bromide is used as a key step to furnish immobilized benzimidazoles. Finally multicomponent condensation of resulted polymer bound benzimidazoles with various aldehydes and 1,3-diones under microwave irradiations provides rapid access for triaza-fluorenes with high purity and excellent yields. Microwave irradiation greatly accelerates the rate of all reactions while polymer support facilitates purifications by simple precipitation technique. This strategy dramatically increases efficiency of overall multistep synthesis.
Hsiao
Ya-Shan
YS
Department of Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan.
Yellol
Gorakh S
GS
Chen
Li-Hsun
LH
Sun
Chung-Ming
CM
D000588:Amines / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D011092:Polyethylene Glycols / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D001372:Aza Compounds; D005449:Fluorenes; D011092:Polyethylene Glycols