623-47-2Relevant articles and documents
Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles
Hu, Linfeng,Cao, Weidi,Wang, Kaixuan,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 13138 - 13141 (2021/12/16)
An enantioselective tandem Friedel-Crafts alkylation/annulation of indoles with diazoacetoacetate enones is realized in one pot. A series of dihydrocarbazoles were obtained in moderate yields with good to excellent ee values by using a RhII/ScIII dual-metallic catalyst system. Control experiments revealed that ScIII is critical to both the alkylation and annulation.
Iodine-Mediated Domino Cyclization for One-Pot Synthesis of Indolizine-Fused Chromones via Metal-Free sp3C-H Functionalization
Fan, Wei-Yu,Feng, Meng-Lin,Gao, Jing-Jing,Wang, Zhuo,Wu, Rui-Xue,Yang, Kai-Rui,Zhang, Han,Zhang, Xiang-Jin,Zhu, Wei,Zhu, Yan-Ping
, (2022/01/12)
An efficient method for the synthesis of new indolizine-fused chromones has been accomplished from ethyl (E)-3-(2-acetylphenoxy)acrylates and pyridines in a "one-pot"manner. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. Moreover, this method can simultaneously construct two molecular fragments of chromone and indolizine. Scale-up experiment and the construction of natural products further prove the practicability of this strategy.
Environment-friendly preparation method of propiolic acid derivatives
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Paragraph 0035-0038, (2020/02/14)
The invention discloses an environment-friendly preparation method of propiolic acid derivatives. The preparation method comprises the following steps: (1) with 2,3-dibromosuccinic acid as a raw material, generating a butynedioic acid salt under alkaline conditions; (2) under an acidic condition, carrying out high-temperature decarboxylation to obtain propiolic acid; and (3) adding corresponding methanol or ethanol into propiolic acid in an extraction solvent, and preparing high-yield propiolate under acidic catalytic conditions under the condition that trimethyl orthoformate or triethyl orthoformate participates in dehydration. In the invention, the propiolic acid preparation method is friendly to environment and high in safety coefficient; and the method provided by the invention can beused for preparing methyl propiolate and ethyl propiolate, and has the advantages of small alcohol consumption, thorough reaction, high yield and easiness in separation.
One-pot mild and efficient synthesis of [1,3]thiazino[3,2-: A] indol-4-ones and their anti-proliferative activity
Rhodes, Steven,Short, Spencer,Sharma, Sidhika,Kaur, Ramneet,Jha, Mukund
supporting information, p. 3914 - 3920 (2019/04/30)
A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-a]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in situ, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4H-[1,3]thiazino[3,2-a]indol-4-one and 8-methyl-2-propyl-4H-[1,3]thiazino[3,2-a]indol-4-one compounds.
Production Of Terephthalic Acid Via Reductive Coupling Of Propiolic Acid Or Propiolic Acid Derivatives
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Paragraph 0035, (2016/10/04)
A method of making terephthalic acid via reductive coupling of two molecules of propiolic acid or propiolic acid derivatives is presented. The reductive coupling can be catalyzed by compounds comprising metals, and propiolic acid or propiolic acid derivatives can be produced from acetylene and carbon dioxide. At least 4 of the 8 carbons in the terephthalic acid are non-fossil-derived.
Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives
Karad, Somnath Narayan,Chung, Wei-Kang,Liu, Rai-Shung
supporting information, p. 13004 - 13007 (2015/08/06)
Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.
Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
Schmidt, Bernd,Riemer, Martin,Schilde, Uwe
supporting information, p. 7602 - 7611 (2016/01/25)
Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
Copper(II)-catalyzed silylation of activated alkynes in water: Diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds
Calderone, Joseph A.,Santos, Webster L.
supporting information, p. 4154 - 4158 (2014/05/06)
Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2PhSiBpin in water at room temperature and open atmosphere, vinylsilanes conjugated to carbonyl groups are synthesized in high yield. A surprising diastereodivergent access to olefin geometry was discovered using a silyl conjugate addition strategy: aldehydes and ketones were Z selective while esters and amides were exclusively transformed into the E products. Dial a diastereomer: The title reaction proceeds through the activation of Me2PhSiBpin in water at room temperature and open atmosphere to produce high yields of vinylsilanes conjugated to carbonyl groups. A surprising diastereodivergent access to olefin geometry was discovered using this silyl conjugate addition strategy: aldehydes were Z selective while esters and amides exclusively delivered the E-configured products.
Aliphatic amino acid biosynthesis inhibitors and a method of synthesizing the same
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Paragraph 0108-0109, (2013/11/05)
The embodiments herein provide a composition and a method of synthesizing a composition comprising an aliphatic amino acid biosynthesis inhibitor having an antifungal activity. The composition comprises 2-oxo-2H-chromen-7-yl propiolate, diethyl-hex-2-en-4-yne-dioate and dinonyl-hex-2-en-4-yne-dioate. The composition inhibits a biosynthesis of an aliphatic amino acid in a fungal biological system. The aliphatic amino acid is selected from a group consisting of leucine, isoleucine and valine. The composition is used with a concentration of 0-200 μg/ml. The method comprises mixing solutions of dicyclohexylcarbodiimide (DCC) and Dimethylaminopyridine (DMAP) with alcohol, acetylene carboxylic acid and dichloromethane to obtain a mixture which is stirred filtered and washed with ether. The solvents are evaporated to obtain a residue that is dissolved in dichloromethane and stirred with a catalyst. The extra solvents are evaporated to obtain the derivative compound and purified by silica gel column chromatography.
Stereoselective synthesis of hex-2-(E)-en-4-yn-1,6-dioates and E,Z-muconic acid diesters via organo-catalyzed self-coupling of propiolates
Ramachandran, P. Veeraraghavan,Rudd, Michael T.,Reddy, M. Venkat Ram
, p. 2547 - 2549 (2007/10/03)
Alkyl propiolate couples with itself in the presence of catalytic DABCO under very mild conditions to provide a quantitative yield of E-hex-2-en-4-yne dioates. Hydrogenation of these enyne dioates using Lindlar catalyst provides the corresponding E,Z-diene dioate, a common structural motif found in an array of natural products.
