163083-16-7Relevant academic research and scientific papers
A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
, p. 3678 - 3686 (2021/05/05)
The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.
Copper-catalyzed double C-S bond formation for the synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes
Sangeetha, Subramani,Sekar, Govindasamy
supporting information, p. 10906 - 10909 (2020/10/02)
An efficient domino process is developed for the synthesis of diversely substituted 2,3-dihydrobenzo[b]thiophenes from 2-iodoketones using a Cu-catalyst and easily available xanthate as a sulfur surrogate in good yields. This domino method has been expanded for the synthesis of 2-acylbenzo[b]thiophenes usingin situgenerated iodine (I2) from by-product KI in high yields. Treatment of xanthate with the copper(ii)-catalyst reduced it to a Cu(i)-catalyst, which initiates the catalytic cycle. A possible mechanism has been proposed based on the results from XPS-analysis, an iodine color test and several other control experiments.
Copper-catalyzed synthesis of 2-acylbenzo[: B] thiophenes from 3-(2-iodophenyl)-1-arylpropan-1-ones and potassium sulfide under aerobic conditions
Zheng, Zhilei,Chen, Liang,Qian, Cheng,Zhu, Xiaoming,Yang, Yuzhong,Liu, Jianbing,Yang, Yuan,Liang, Yun
, p. 8020 - 8024 (2018/11/23)
A method was developed for the synthesis of 2-acylbenzo[b]thiophenes via a copper-catalyzed sulfuration of 3-(2-iodophenyl)-1-arylpropan-1-ones with K2S under aerobic conditions. Mechanistically, this procedure was proved to involve the formati
Synthesis of 2-Acylbenzo[b]thiophenes via Cu-Catalyzed α-C-H Functionalization of 2-Halochalcones Using Xanthate
Sangeetha, Subramani,Sekar, Govindasamy
supporting information, p. 1670 - 1673 (2017/04/11)
An efficient protocol is described for the synthesis of 2-acylbenzo[b]thiophenes from easily accessible 2-iodochalcones through α-C-H functionalization using Cu(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)ethanone, which is a known pre-mRNA splicing modulator.
Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes
Ushijima, Sousuke,Dohi, Souya,Moriyama, Katsuhiko,Togo, Hideo
scheme or table, p. 1436 - 1442 (2012/03/09)
Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.
Synthesis of (4-chlorophenyl)-(1-oxo-1λ4-benzo[b]thien-2-yl)methanone and study of its reactivity towards sulfur- and oxygen-containing nucleophiles
Pouzet, Pascale,Erdelmeier, Irene,Dansette, Patrick M.,Mansuy, Daniel
, p. 14811 - 14824 (2007/10/03)
(4-Chlorophenyl)-(1-oxo-1λ4-benzo[b]thien-2-yl)methanone 2a was synthesized by oxidation of the corresponding benzo[b]thiophene derivative 2 with the oxidative system H2O2/TFA. This benzo[b]thiophene sulfoxide undergoes Michael-type nucleophilic addition of sulfur- and oxygen-containing nucleophiles either under basic conditions leading to 2,3-dihydro-3- substituted-benzo[b]-thiophene 1-oxides or in acidic media leading then to rearomatized 3-substituted-benzo[b]thiophenes. This method provides an easy two-step functionalization of 2-acyl-benzo[b]thiophene derivatives.
