1170724-05-6Relevant articles and documents
Synthesis of novel artesunate-benzothiophene and artemisinin-benzothiophene derivatives
Kavak, Emrah,Kivrak, Arif,Ozok, Omruye
supporting information, (2021/05/27)
Natural products are used for the treatment of a variety of diseases for many years. Last decades, design and synthesis of novel biologically active hybrid molecules including natural product is gained big importance due to their unique and new biological
Synthesis of (Thio)Furan-Fused Phospholes via Phosphonation Cyclization and a Base-Promoted Phospha-Friedel-Crafts Reaction
Chen, Siyu,Ding, Haixin,Hua, Yuhui,Huang, Haiyang,Li, Chenchen,Liu, Fen,Song, Xian-Rong,Xiao, Qiang,Yuan, Chengxiong
, (2022/02/07)
Herein, we developed a novel strategy for synthesizing ladder (thio)furan-fused phospholes via intermolecular phosphonation cyclization and a base-promoted phospha-Friedel-Crafts reaction under mild conditions. The starting substrates are readily available phosphinic acids and easy-to-handle alkynes. The details of the reaction mechanism were further rationalized using theoretical calculations. This protocol can be widely applied to synthesize furan- and thiofuran-fused phospholes as well as the corresponding large π-extended derivatives, which are of great interest in the domain of organic functional materials.
BCl3-Induced Annulative Oxo- and Thioboration for the Formation of C3-Borylated Benzofurans and Benzothiophenes
Warner, Andrew J.,Churn, Anna,McGough, John S.,Ingleson, Michael J.
supporting information, p. 354 - 358 (2016/12/30)
BCl3-induced borylative cyclization of aryl-alkynes possessing ortho-EMe (E=S, O) groups represents a simple, metal-free method for the formation of C3-borylated benzothiophenes and benzofurans. The dichloro(heteroaryl)borane primary products can be protected to form synthetically ubiquitous pinacol boronate esters or used in situ in Suzuki–Miyaura cross couplings to generate 2,3-disubstituted heteroarenes from simple alkyne precursors in one pot. In a number of cases alkyne trans-haloboration occurs alongside, or instead of, borylative cyclization and the factors controlling the reaction outcome are determined.
Pd/phenanthroline-catalyzed arylative cyclization of o-(1-alkynyl)thioanisoles: Synthesis of 3-arylated benzo[b]thiophenes
Yamauchi, Takayuki,Shibahara, Fumitoshi,Murai, Toshiaki
supporting information, p. 2945 - 2948 (2016/07/06)
The arylative cyclization of o-(1-alkynyl)thioanisoles with aryl iodides in the presence of catalytic amounts of [Pd(phen)2][PF6]2resulted in the efficient formation of 3-arylated benzo[b]thiophenes, and a range of aryl iodides with electron-donating or -withdrawing groups could be used. While this reaction proceeded in the presence of aromatic and aliphatic groups on the terminal alkynyl carbon atom, silyl and alkoxycarbonyl groups hampered the reaction. Furthermore, this method could be extended to the synthesis of 3-arylated indoles from N,N-dimethyl-o-(1-alkynyl)aniline. All these reactions proceeded smoothly via cleavage of the carbon-heteroatom bond. In addition to the desired cyclization products, the use of a o-(hydroxypropyl)phenylmethyl substituent on the sulfur atom afforded isochroman, which should be formed by the intramolecular attack of a hydroxy group onto the benzylic carbon atom.
