264142-55-4Relevant academic research and scientific papers
Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes
Chen, Xinyu,Zhang, Zhebing,Sun, Tao,Cai, Haokun,Gao, Yuzhen,Cai, Tao,Shang, Tianbo,Luo, Yanjuan,Yu, Guoqi,Shen, Hualiang,Wu, Guofeng,Hei, Yanlin,Li, Enmin,Fan, Gang
supporting information, (2022/01/14)
An efficient and practical protocol for the Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles towards valuable 3-halobenzo[b]thiophenes is described. Structurally diverse 3-halobenzothiophenes were obtained in good to excellent yields
Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling
Cho, Chul-Hee,Jung, Dai-Il,Neuenswander, Benjamin,Larock, Richard C.
experimental part, p. 501 - 510 (2011/10/31)
For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr3.
A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization
Cho, Chul-Hee,Jung, Dai-Il,Larock, Richard C.
supporting information; experimental part, p. 6485 - 6488 (2011/02/22)
A formal total synthesis of the benzothiophene selective estrogen receptor modulator (SERM) desketoraloxifene and analogs has been accomplished from alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I2. This approa
A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents
Flynn, Bernard L.,Verdier-Pinard, Pascal,Hamel, Ernest
, p. 651 - 653 (2007/10/03)
Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylpnenyl sulfides which re
