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Volumn , Issue 4, 2009, Pages 628-632

An efficient, regioselective, versatile synthesis of N-fused 2- and 3-aminoimidazoles via Ugi-type multicomponent reaction mediated by zirconium(IV) chloride in polyethylene glycol-400

Author keywords

Multicomponent reaction; N heterocycles; Polyethylene glycol; Regioselective synthesis; Zirconium(IV) chloride

Indexed keywords


EID: 62249186769     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087915     Document Type: Article
Times cited : (86)

References (38)
  • 31
    • 35048880551 scopus 로고    scopus 로고
    • For greener use of PEG-400 as solvent, see: (a) Han, W.; Liu, C.; Jin, Z.-L. Org. Lett. 2007, 9, 4005.
    • For greener use of PEG-400 as solvent, see: (a) Han, W.; Liu, C.; Jin, Z.-L. Org. Lett. 2007, 9, 4005.
  • 33
    • 41349104872 scopus 로고    scopus 로고
    • For significant use of ZrCl4, see: Review paper: Smitha, G.; Chandrasekhar, S.; Reddy, C. S. Synthesis 2008, 829.
    • (a) For significant use of ZrCl4, see: Review paper: Smitha, G.; Chandrasekhar, S.; Reddy, C. S. Synthesis 2008, 829.
  • 36
    • 62249163074 scopus 로고    scopus 로고
    • Representative Experimental Procedure for the Synthesis of N-tert-Butyl-2-(4-chlorophenyl)imidazo[1,2-a] pyridin-3-amine (Table 2, entry 1, To a mixture of 2-aminopyridine (0.19 g, 2 mmol) and 4-chlorobenzaldehyde (0.28 g, 2 mmol) in PEG-400 (2 mL, tert-butyl isocyanide (0.17 g, 2 mmol) and ZrCl4 (47 mg, 10 mol, were added. The mixture was allowed to stir at 50°C under open air. After completion of the reaction (4.5 h, monitored by TLC, the resulting mixture was extracted with EtOAc and washed with H2O. The organic layer was dried over anhyd Na2SO4, filtered and concentrated under reduced pressure. The column chromatographic purification of crude product over silica gel (mesh size: 60-120) eluting with EtOAc-hexane (1:1.5) afforded N-tert-butyl-2-(4-chlorophenyl)imidazo-[1,2-a] pyridin-3-amine (0.48 g, 85, white solid; mp 146-149°C. MS ESI, m/z, 300 [M, 1
    • 3: C, 68.11; H, 6.05; N, 14.02. Found: C, 67.89; H, 6.07; N, 13.99. All reactions (Tables 1- 3) were carried out following this procedure.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.