A new laccase-catalyzed domino process and its application to the efficient synthesis of 2-aryl-1H-benzimidazoles

Tetrahedron Letters

Volumn 52, Issue 5, 2011, Pages 605-608

  Leutbecher, Heiko ^a   Constantin, Mihaela Anca ^a   Mika, Sabine ^a   Conrad, Jürgen ^a   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Aerobic oxidation; Domino reactions; Laccase; N Heterocycles

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 ARYL 1H BENZIMIDAZOLE; BENZALDEHYDE; BENZIMIDAZOLE DERIVATIVE; LACCASE; OXIDIZING AGENT; OXYGEN; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; DOMINO REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME MECHANISM; OXIDATION KINETICS;

EID: 78651102272     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.145     Document Type: Article

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49. General procedure for synthesis of 5a-g: 1.0 equiv 6 (0.2 mmol) [6b (0.13 mmol), 6c (0.18 mmol), 6d (0.11 mmol), respectively] and 1.0 equiv o-phenylenediamine (1a) were dissolved in phosphate buffer (14 mL, 0.2 M, pH 6.0) or a phosphate buffer/methanol mixture (see Table 1). 31 U laccase from Agaricus bisporus were added. The reaction mixture was shaken with a shaking frequency of 850 rpm using a liquid phase synthesis system 'Synthesis 1' (Heidolph) for 3-18 h (see Table 1) at room temperature under air until the substrates had been fully consumed. Alternatively, the reaction could be performed using a magnetic stirrer at high stirring speed. The reaction mixture was saturated with sodium chloride and filtered through a Büchner funnel. For isolation of products 5a-d 2 M KOH (1 mL) was added before filtration. The filter cake was washed with 15% sodium chloride solution (20 mL) and water (2 mL) and dried at room temperature to yield pure heterocycles 5a-g (NMR). Analytically pure compounds could be obtained via recrystallization.
50. +] 274.0412; found 274.0416.