415680-03-4Relevant academic research and scientific papers
Environmentally benign process for the synthesis of 2,3-disubstituted benzo[b]thiophenes using electrophilic cyclization
Kim, Seoyoung,Dahal, Nikesh,Kesharwani, Tanay
, p. 4373 - 4376 (2013)
We have developed a greener process for the synthesis of 2,3-disubstituted benzo[b]thiophenes using electrophilic cyclization as a key step. Our method not only employs an environmentally friendly solvent ethanol, but also utilizes safe and inexpensive in
Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes
Kesharwani, Tanay,Kornman, Cory,Tonnaer, Amanda,Hayes, Amanda,Kim, Seoyoung,Dahal, Nikesh,Romero, Ralf,Royappa, Andrew
, p. 2973 - 2984 (2018/05/23)
A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed met
Efficient synthesis of 3-benzoyl Benzo[b]thiophenes and raloxifene via Mercury(II)-Catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides
Wen, Shi-Ming,Lin, Cheng-Han,Chen, Chin-Chau,Wu, Ming-Jung
, p. 2493 - 2499 (2018/04/16)
The unique selective estrogen receptor modulator, Raloxifene (1), and antitubulin agent 2 were synthesized through the key intermediate, 4-methoxybenzyl 2-bromo-4-methoxyphenyl sulfoxide (6), respectively. It was found that compared with the o-sulfanyl aryl bromides, the sulfinyl group at ortho position accelerated the Sonogashira coupling reaction of aryl bromides. Thus, compound 6 was coupled with 3,4,5-trimethoxyphenyl acetylene, followed by mercury-catalyzed cyclization reaction afford compound 2 in 79% overall yield. Raloxifene (1) was prepared from compound 6 in four steps and 33% overall yield via coupling reaction with 1-trimethylsily-2-(4-tert-butyldimethylsiloxy)phenylethyne, mercury-catalyzed cyclization reaction, alkylation and demethylation.
Mercury(II)-catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides provides 3-acylbenzo[b]thiophenes
Lin, Cheng-Han,Chen, Chin-Chau,Wu, Ming-Jung
supporting information, p. 2578 - 2581 (2013/03/14)
Ring cyclization: A mercury-catalyzed cyclization reaction to provide 3-benzoylbenzo[b]thiophenes was achieved in good yields by treatment of 2-alkynylphenyl alkyl sulfoxides with mercury chloride and 2,3-dichloro-5,6- dicyano-1,4-benzoquinone (DDQ) in be
Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo[b]thiophenes
Lu, Wen-Der,Wu, Ming-Jung
, p. 356 - 362 (2007/10/03)
Reaction of 2-alkynylthioanisoles 3 with 2 equiv of CuX2 (X=Br or Cl) in refluxing CH3CN for 2.5 h gave the 2-substituted 3-halobenzo[b]thiophenes 4 in good yields.
Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling anphilic cyclization of terminal acetylenes
Yue, Dawei,Larock, Richard C.
, p. 1905 - 1909 (2007/10/03)
2,3-Disubstituted benzo[b]thiophenes have been prepared in excellent yields via coupling of terminal acetylenes with commercially available o-iodothioanisole in the presence of a palladium catalyst and subsequent electrophilic cyclization of the resulting
