107209-64-3Relevant academic research and scientific papers
Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles
He, Xiang-Kui,Li, Lei,Lu, Juan,Xuan, Jun,Ye, Hai-Bing
, (2021/11/27)
An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.
Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles
He, Yimiao,Wang, Xuelian,Xiao, Jun-An,Pang, Jinying,Gan, Chunfang,Huang, Yanmin,Huang, Chusheng
, p. 3036 - 3040 (2018/02/06)
A metal-free, mild and efficient protocol for the construction of aroylated N-heterocycles via radical cascade aroylation of phenyl or vinyl isocyanides with aromatic aldehydes has been developed. Both phenanthridine and isoquinoline derivatives are delivered quickly in moderate to good yields with high regioselectivity.
Synthesis of 6-aroyl phenanthridines by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols
Nie, Ziyi,Ding, Qiuping,Peng, Yiyuan
, p. 8350 - 8357 (2016/12/02)
A practical method for the synthesis of 6-aroyl phenanthridine derivatives by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols is described. In addition, this cyclization could be occurred by using toluene as aroyl source. The procedure tolerates various functional groups under simple conditions. A single-electron-transfer pathway is proposed according to mechanistic studies.
Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides
Liu, Jie,Fan, Chao,Yin, Hongyu,Qin, Chu,Zhang, Guoting,Zhang, Xu,Yi, Hong,Lei, Aiwen
, p. 2145 - 2147 (2014/02/14)
A silver catalysed synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This reaction provided a novel method to realize C1 insertion via a radical process and various functional groups were well-tolerated. The Royal Society of Chemistry.
6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS)
Leifert, Dirk,Daniliuc, Constantin Gabriel,Studer, Armido
, p. 6286 - 6289 (2014/01/17)
Readily accessible 2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imidoyl radicals. Initiation of the radical chain reaction is best achieved with small amounts of FeCl3 (0.4 mol %), and the commercially available and cheap tBuOOH is used as the oxidant.
Cycloaddition Reactions of Ketoimines. Part II. Synthesis of Substituted Phenanthridines and Cyclopentaquinolines
Lucchini, Vittorio,Prato, Maurizio,Scorrano, Giafranco,Tecilla, Paolo
, p. 1135 - 1139 (2007/10/02)
Substituted 4-benzoyl-3a,4,5,9b-tetrahydro-3H-cyclopentaquinolines 3 and 6-benzoyl-5,6,6a,7,8,10a-hexahydrophenanthridines 10 are obtained through Lewis acid catalyzed addition of 1-phenyl-2-arylamino-2-methoxyethanones 2 to cyclopentadienes and 1,3-cy
