110166-71-7Relevant 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.
Tetraalkynylstannanes in the Stille cross coupling reaction: a new effective approach to arylalkynes
Levashov, Andrey S.,Buryi, Dmitrii S.,Goncharova, Olga V.,Konshin, Valeriy V.,Dotsenko, Victor V.,Andreev, Alexey A.
supporting information, p. 2910 - 2918 (2017/04/14)
The Stille-type cross coupling reaction with tetraalkynylstannanes was studied in detail for the first time. The reaction provides a simple and effective route towards a variety of arylalkynes. The advantages and limitations of the proposed procedure are discussed.
Oxypalladation Initiating the Oxid-ative Heck Reaction with Alkenyl -Alcohols: Synthesis of Isocoumarin–Alkanones
Zheng, Meifang,Huang, Liangbin,Tong, Qizhen,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 663 - 667 (2017/01/18)
Highly regioselective nucleopalladation for the oxidative coupling of internal alkynes with alkenyl alcohols by using green and low-costing oxygen as the sole oxidant was investigated. This one-pot cascade cyclization proceeds through Pd-catalyzed intramolecular C–O bond cyclization, insertion of nonbiased alkenyl alcohols, β-H elimination, and reinsertion of a HPdX species, which is finally transferred to the target ketones. This method has the advantages of mild conditions, good functional group tolerance, and can be performed with unactivated alkenes to afford isocoumarin derivatives.
Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
Faizi, Darius J.,Issaian, Adena,Davis, Ashlee J.,Blum, Suzanne A.
supporting information, 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
Sunlight promoted palladium catalysed Mizoroki-Heck, Suzuki-Miyaura and Sonogashira reactions
Chaudhary, Anju R.,Bedekar, Ashutosh V.
, p. 6100 - 6103,4 (2020/08/20)
The palladium catalysed Mizoroki-Heck, Suzuki-Miyaura and Sonogashira reactions were successfully carried out under irradiation with sunlight. The Heck reaction gives considerable amount of Z product due to photochemical isomerization of initially formed E alkenes. Reaction of methyl 2-iodobenzoate with acrylamide under solar condition furnished 2H-2-benzazepine-1,3-dione rather than the expected derivative of cinnamate while the same reaction with ethyl 2-iodobenzoate gave the desired cinnamide.
Exploratory studies on the reaction between iodoarenes and acetylenes: One-pot, Pd-[Bmim][BF4] catalyzed preparation of trianisylethylene
Barros, Jose C.,Souza, Andrea L. F.,Da Silva, Joaquim F. M.,Antunes
scheme or table, p. 549 - 553 (2012/01/13)
The reaction between iodoarenes and acetylenes mediated by palladium was studied, showing selectivity changes based on the nature of the substituent. A new, phosphine-, copper-, and amine-free methodology was developed, in which the synthesis of trianisylethylene from 4-iodoanisole and trimethylsilylacetylene was promoted presumably by an N-heterocyclic-carbene derived from an ionic liquid and a palladium salt, using ethanol as the hydrogen source. Graphical Abstract: [Figure not available: see fulltext.]
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.
Palladhim-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide
Kim, Hyunseok,Lee, Phil Ho
scheme or table, p. 2827 - 2832 (2010/03/26)
Palladium-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide have been developed. A variety of α,β-ynoic acids were readily decarboxylated in the presence of
Benzamidoaldehydes and their use as cysteine protease inhibitors
-
, (2008/06/13)
Compounds of the formula where R1, R2, R3, X and n are as defined in the description, are inhibitors of cysteine protease.
