摘要
以α-氨基酸与邻苯二胺在微波辐射下反应合成了α-氨基取代苯并咪唑(1～5).1-(1H-苯并[d]咪唑-2-基)乙胺(1)与溴丁烷反应可形成单丁基、二丁基、三丁基取代产物1a～1d,1的氨基经Boc保护,N-烷基化后制备咪唑环上的N-烷基化产物1i～1g.制备的氨基取代咪唑与Ru(II)化合物原位组成催化体系,考察了其在取代苯乙酮的氢转移反应中的催化活性.结果表明RuCl2(PPh3)3与各配体组成的催化剂均有较好的催化活性,含有NH2基团的α-氨基取代苯并咪唑化合物参与的催化体系催化活性最好,TOF(Turnover frequency)可达到40200 h-1.
A series of a-amino-benzimidazole derivatives 1-5 were synthesized by reaction of a-amino acid with o-phenylenediamine under microwave irradiation. 1-（1H-Benzo[d]imidazol-2-yl）ethanamine （1） reacted with bromobutane forming mono-butyl, dibutyl and tributyl substituted benzimidazole la^ld; and the N-alkylated derivatives 1i-1g were syn
thesized by protection of amine group by Boc and then N-alkylation. The catalytic capability of the catalyst generated in situ from Ru（II） compound and obtained benzimidazole derivatives were evaluated in the transfer hydrogenation of ketones using iso-PrOH as hydrogen donor and solvent. The results revealed that catalyst generated in situ from RUC1E（PPh3）3 and ligands had moderate to high activity. The catalyst system with a-amino-benzimidazole derivative containing NH2 group is the most active and the highest TOF （turnover frequency） was up to 40200 h-1.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2012年第7期1247-1254,共8页
Chinese Journal of Organic Chemistry
基金
河北省自然科学基金(No.B2011202087)资助项目~~
关键词
氨基酸
苯并咪唑
N-烷基化
微波
钌络合物
酮
氢转移反应
amino acid
benzimidazole
N-alkylation
microwave
Ru（II） complex
ketone
transfer hydrogenation
