Zi-Hong Zhou, Yong-Bo Xu, Shuming Wu, Wei-Jian Ling, Lei Zhang, Zhongqing Wang
{"title":"NaBH4-FeCl2选择性硝基还原酯取代硝基芳烃","authors":"Zi-Hong Zhou, Yong-Bo Xu, Shuming Wu, Wei-Jian Ling, Lei Zhang, Zhongqing Wang","doi":"10.1055/s-0042-1756457","DOIUrl":null,"url":null,"abstract":"This work aimed to explore a novel protocol for selective reduction of the nitro group on the aromatic ring while remaining the ester group unaffected. In this study, NaBH4-FeCl2 was disclosed as a key reductant in the process. NaBH4-FeCl2-mediated reduction showed high chemoselectivity, gave the desired products in magnificent yield (up to 96%), and was applied to synthesize a key intermediate of vilazodone (an antidepressant drug) on a hectogram scale in a total yield of 81% (two steps). The protocol is practical, and capable of synthesis of a range of aromatic amines, especially those with ester substituted in the ring.","PeriodicalId":19767,"journal":{"name":"Pharmaceutical Fronts","volume":"16 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2022-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Selective Nitro Reduction of Ester Substituted Nitroarenes by NaBH4-FeCl2\",\"authors\":\"Zi-Hong Zhou, Yong-Bo Xu, Shuming Wu, Wei-Jian Ling, Lei Zhang, Zhongqing Wang\",\"doi\":\"10.1055/s-0042-1756457\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"This work aimed to explore a novel protocol for selective reduction of the nitro group on the aromatic ring while remaining the ester group unaffected. In this study, NaBH4-FeCl2 was disclosed as a key reductant in the process. NaBH4-FeCl2-mediated reduction showed high chemoselectivity, gave the desired products in magnificent yield (up to 96%), and was applied to synthesize a key intermediate of vilazodone (an antidepressant drug) on a hectogram scale in a total yield of 81% (two steps). The protocol is practical, and capable of synthesis of a range of aromatic amines, especially those with ester substituted in the ring.\",\"PeriodicalId\":19767,\"journal\":{\"name\":\"Pharmaceutical Fronts\",\"volume\":\"16 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2022-09-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Pharmaceutical Fronts\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/s-0042-1756457\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Pharmaceutical Fronts","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0042-1756457","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Selective Nitro Reduction of Ester Substituted Nitroarenes by NaBH4-FeCl2
This work aimed to explore a novel protocol for selective reduction of the nitro group on the aromatic ring while remaining the ester group unaffected. In this study, NaBH4-FeCl2 was disclosed as a key reductant in the process. NaBH4-FeCl2-mediated reduction showed high chemoselectivity, gave the desired products in magnificent yield (up to 96%), and was applied to synthesize a key intermediate of vilazodone (an antidepressant drug) on a hectogram scale in a total yield of 81% (two steps). The protocol is practical, and capable of synthesis of a range of aromatic amines, especially those with ester substituted in the ring.