88180-65-8Relevant academic research and scientific papers
Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters
Norseeda, Krissada,Chaisan, Nattawadee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
, p. 16222 - 16236 (2019/12/25)
4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.
Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
Faizi, Darius J.,Issaian, Adena,Davis, Ashlee J.,Blum, Suzanne A.
, p. 2126 - 2129 (2016/03/05)
A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organobor
Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: Synthesis of 1-alkoxyisoquinolines and isoquinolones
Li, Jim,Chen, Lijing,Chin, Elbert,Lui, Alfred S.,Zecic, Hasim
experimental part, p. 6422 - 6425 (2010/12/25)
A facile synthesis of a series of 1-alkoxyisoquinolines and (2H)-isoquinolones by an intramolecular 6-endo-dig cyclization of ortho-alkynylbenzonitriles in the presence of a catalytic amount of hydrido(dimethylphosphinous acid-κP)[hydrogen bis(dimethylphosphinito- κP)]platinum(II) in various alcohols at 65-90 °C is described for the first time.
Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers
Kusama, Hiroyuki,Funami, Hideaki,Iwasawa, Nobuharu
, p. 2014 - 2024 (2008/02/11)
A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the PtCl 2-catalyzed reaction of o-ethynylbenzoates or benzothioates with vinyl ethers. Treatment of o-alkynylbenzoate derivatives with PtCl2 generated the platinum(II)-containing carbonyl ylides as a key reactive intermediate and these species reacted with vinyl ethers to give substituted naphthalenes in good yields. The presence of the platinum-containing carbonyl ylide was confirmed by NMR analyses of the mixture of o-ethynylbenzoate and [PtCl2(H2C=CH2)]2. Furthermore, it was suggested that the naphthalene derivatives were produced by [3+2] cycloaddition of the ylide species with vinyl ethers, followed by 1,2-alkyl migration of the generated platinum-carbene intermediates. Georg Thieme Verlag Stuttgart.
Platinum(II)-Catalyzed Reaction of 2-Alkynylbenzoates or Benzothioates with Vinyl Ethers: A Concise Method for Synthesis of 1-Acyl-4-alkoxy- or 1-Acyl-4-alkylsulfanylnaphthalene Derivatives
Kusama, Hiroyuki,Funami, Hideaki,Takaya, Jun,Iwasawa, Nobuharu
, p. 605 - 608 (2007/10/03)
(Matrix presented) A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the reaction of o-ethynylbenzoates or benzothioates with vinyl ethers, in the presence of a catalytic amount of PtCl2. It is proposed that the reaction proceeds through [3 + 2]-cycloaddition of the platinum-containing carbonyl ylides followed by 1,2-alkyl migration.
