- I2/TBHP promoted oxidative C–N bond formation at room temperature: Divergent access of 2-substituted benzimidazoles involving ring distortion
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A new ‘one pot’ tandem synthesis of 2-substituted benzimidazoles has been developed from 2-aminobenzyl alcohol/2-aminobenzamide and different coupling partners (nitriles, aldehydes and 1,3-diketones) via iodine and TBHP promoted oxidative ring contraction. The present strategy involves sequential C–N bond formation, cyclization, subsequent ring contraction and dehydrogenation to afford various medicinally important benzimidazole derivatives in moderate to good yields. This operationally simple synthetic approach proceeds at room temperature under base-free condition, broadly applicable to a wide array of nitriles and aldehydes bearing oxidation prone functional groups and noteworthy to mention that various acyclic 1,3-diketones undergo selective C–C bond cleavage leading to 2-alkyl benzimidazoles under mild condition.
- Saha, Moumita,Das, Asish R.
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supporting information
p. 2520 - 2525
(2018/05/31)
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- CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles
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(Figure Presented) CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazol
- Deng, Xiaohu,McAllister, Heather,Mani, Neelakandha S.
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supporting information; experimental part
p. 5742 - 5745
(2009/12/06)
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