Microwave Controlled Reductive Cyclization: A Selective Synthesis of Novel Benzimidazole-alkyloxypyrrolo[1,2-a]quinoxalinones

被引:22
作者
Dhole, Sandip [1 ]
Selvaraju, Manikandan [1 ]
Maiti, Barnali [1 ]
Chanda, Kaushik [1 ]
Sun, Chung-Ming [1 ,2 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
[2] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 80708, Taiwan
关键词
polymer supported; microwave-assisted; pyrroloquinoxalinones; reductive cyclization; DIVERGENT SYNTHESIS; INHIBITORS; POTENT; DISCOVERY; SUPPORT; QUINOXALINONES; BENZIMIDAZOLYL; SCHIZOPHRENIA; IRRADIATION; LIBRARIES;
D O I
10.1021/acscombsci.5b00010
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient cascade synthesis of novel benzimidazole linked alkyloxypyrrolo[1,2-a]quinoxalinones was explored on soluble polymer support under micro-Wave irradiation. Two exclusive protocols have been developed for the partial and reductive cyclization by Controlling the microwave energy, Commencing from the smile substrate, ortho nitro, pyrrol: carboxylates, N-hydroxy pyrroloquinoxalinones were obtained by,, partial reductive cyclization (60 degrees C, 7 min), and the synthesis of pyrroloquinoxalinones was accomplished by full reductive, cyclization (85 degrees C, 12 min). This method represents the first synthesis N-hydroxy pyrroloquinoxalinones using Pd/C and ammonium formate as reducing agents: Further employing a variety Of alkyl bromides, the obtained pyrroloquinoxalinones were transformed to their corresponding O-, and N-alkylated analogues to deliver the diversified, novel molecular entities.
引用
收藏
页码:310 / 316
页数:7
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