Dhole Sandip, Selvaraju Manikandan, Maiti Barnali, Chanda Kaushik, Sun Chung-Ming
†Department of Applied Chemistry, National Chiao Tung University, 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
‡Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100, Shih-Chuan first Road, Kaohsiung 807-08, Taiwan.
ACS Comb Sci. 2015 May 11;17(5):310-6. doi: 10.1021/acscombsci.5b00010. Epub 2015 Apr 21.
An efficient cascade synthesis of novel benzimidazole linked alkyloxypyrrolo[1,2-a]quinoxalinones was explored on soluble polymer support under microwave irradiation. Two exclusive protocols have been developed for the partial and full reductive cyclization by controlling the microwave energy. Commencing from the same substrate, ortho nitro pyrrol carboxylates, N-hydroxy pyrroloquinoxalinones were obtained by partial reductive cyclization (60 °C, 7 min), and the synthesis of pyrroloquinoxalinones was accomplished by full reductive cyclization (85 °C, 12 min). This method represents the first synthesis of 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.
在微波辐射下，在可溶性聚合物载体上探索了一种高效的新型苯并咪唑连接的烷氧基吡咯并[1,2 - a]喹喔啉酮的级联合成方法。通过控制微波能量，开发了两种用于部分和完全还原环化的独特方案。从相同的底物邻硝基吡咯羧酸盐开始，通过部分还原环化（60°C，7分钟）获得N - 羟基吡咯并喹喔啉酮，通过完全还原环化（85°C，12分钟）完成吡咯并喹喔啉酮的合成。该方法代表了首次使用Pd/C和甲酸铵作为还原剂合成N - 羟基吡咯并喹喔啉酮。进一步使用各种烷基溴，将得到的吡咯并喹喔啉酮转化为其相应的O - 和N - 烷基化类似物，以提供多样化的新型分子实体。
