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2-(Methoxycarbonyl)ethyl as a Removable N-Protecting Group: Synthesis of Indoloisoquinolinones by Pd(II)-Catalyzed Intramolecular Diamination of Alkynes
Organic Letters ( IF 4.9 ) Pub Date : 2015-03-13 00:00:00 , DOI: 10.1021/acs.orglett.5b00526 Tu M. Ha 1 , Bo Yao 1 , Qian Wang 1 , Jieping Zhu 1
Organic Letters ( IF 4.9 ) Pub Date : 2015-03-13 00:00:00 , DOI: 10.1021/acs.orglett.5b00526 Tu M. Ha 1 , Bo Yao 1 , Qian Wang 1 , Jieping Zhu 1
Affiliation
Pd(II)-catalyzed double cyclization of 1,2-diarylethynes bearing an N-methyl-N-[2-(methoxycarbonyl)ethyl]amino and an aminocarbonyl group at the ortho positions of the two aromatic rings afforded the tetracyclic N-[2-(methoxycarbonyl)ethyl]indoloisoquinolinones in good to excellent yields. The N-[2-(methoxycarbonyl)ethyl] group is readily removed under basic conditions (DBU, DMF, 120 °C) to afford the corresponding tetracycles with a free indolyl nitrogen in excellent yields. The 2-(methoxycarbonyl)ethyl as a removable N-protecting group is illustrated in other Pd(II)- and Pd(0)-catalyzed and selenium-mediated transformations.
中文翻译:
2-(甲氧羰基)乙基作为可移动的N保护基:钯(II)催化炔烃分子内缩合反应合成吲哚异喹啉酮
Pd(II)催化的在两个芳环的邻位带有N-甲基-N- [2-(甲氧基羰基)乙基]氨基和氨基羰基的1,2-二芳基乙炔的双环化反应得到四环N- [ 2-(甲氧基羰基)乙基]吲哚异喹啉酮类化合物的收率高至优异。在碱性条件(DBU,DMF,120°C)下,N- [2-(甲氧羰基)乙基]基很容易被除去,以极好的收率得到相应的带有游离吲哚基氮的四环。在其他Pd(II)和Pd(0)催化和硒介导的转化中说明了作为可移动N保护基的2-(甲氧羰基)乙基。
更新日期:2015-03-13
中文翻译:
2-(甲氧羰基)乙基作为可移动的N保护基:钯(II)催化炔烃分子内缩合反应合成吲哚异喹啉酮
Pd(II)催化的在两个芳环的邻位带有N-甲基-N- [2-(甲氧基羰基)乙基]氨基和氨基羰基的1,2-二芳基乙炔的双环化反应得到四环N- [ 2-(甲氧基羰基)乙基]吲哚异喹啉酮类化合物的收率高至优异。在碱性条件(DBU,DMF,120°C)下,N- [2-(甲氧羰基)乙基]基很容易被除去,以极好的收率得到相应的带有游离吲哚基氮的四环。在其他Pd(II)和Pd(0)催化和硒介导的转化中说明了作为可移动N保护基的2-(甲氧羰基)乙基。