1604-29-1Relevant articles and documents
Total Synthesis of (±)-Aspergilline A
Nakhla, Mina C.,Wood, John L.
, p. 18504 - 18507 (2017)
The total synthesis of (±)-aspergilline A (1) is described. Key features of the synthesis include pyrrolinone formation via reaction of an intermediate propargyl amine with a methyl malonyl chloride derived ammonium enolate and a formal [3+2] cycloaddition between an imidate and cyclopropenone.
Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N -Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach
Alduhaish, Osamah,Varala, Ravi,Adil, Syed Farooq,Khan, Mujeeb,Siddiqui, Mohammed Rafiq H.,Alwarthan, Abdulrhman,Alam, M. Mujahid
, (2020/10/02)
An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.
DIHYDROOROTATE DEHYDROGENASE INHIBITORS
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Page/Page column 75; 92, (2020/10/28)
Disclosed are compounds, compositions and methods for treating diseases, disorders, or medical conditions that are affected by the modulation of DHODH. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, X, and Y are defined herein.
BTK Inhibitors and uses thereof
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Paragraph 1225-1230, (2020/05/02)
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence
Lin, Hsin-Hui,Chiang, Tai-Ching,Wu, Rong-Xuan,Chang, Yi-Mei,Wang, Hao-Wen,Liu, Ssu-Ting,Yeh, Ming-Chang P.
supporting information, (2019/02/07)
A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).
SUBSTITUTED 5-CYANOINDOLE COMPOUNDS AND USES THEREOF
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Paragraph 00249, (2019/01/10)
A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for the treatment of lysine (K)-specific demethylase 1A (LSD1) - mediated diseases or disorders, Formula (I), wherein R1, R2, R3, R4, and R5 are as defined herein.
Robust Silver(I) Catalyst for the Carboxylative Cyclization of Propargylic Alcohols with Carbon Dioxide under Ambient Conditions
Song, Qing-Wen,He, Liang-Nian
supporting information, p. 1251 - 1258 (2016/04/26)
Inspired by the bulkier bis(triphenylphosphine)-silver cation-induced mechanism of propargylic alcohols and carbon dioxide through the alkyl carbonate intermediate, a robust dual-component catalytic system consisting of silver acetate and tetraheptylammonium bromide was rationally developed for the synthesis of α-methylene cyclic carbonates under ambient conditions without employing any additional organic base and ligand. This is one of the most effective catalysts reported to date for this conversion, with a very high turnover number of up to 6024, probably due to the synergistic effect of Lewis basic and Lewis acidic species for the activation of both propargylic alcohol and carbon dioxide by the formation of the alkyl carbonate with a bulkier counterion. Notably, this catalyst also worked well for the carboxylative cyclization of propargylic amines with carbon dioxide with the highest turnover number of 544.
Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
Lepronier, Aymeric,Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard,Clavier, Herve
supporting information, p. 631 - 642 (2016/02/27)
Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.
Convenient synthesis of allenylphosphoryl compounds: Via Cu-catalysed couplings of P(O)H compounds with propargyl acetates
Shen, Ruwei,Luo, Bing,Yang, Jianlin,Zhang, Lixiong,Han, Li-Biao
supporting information, p. 6451 - 6454 (2016/05/24)
A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.
Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones
Sekine, Kohei,Kobayashi, Ryo,Yamada, Tohru
supporting information, p. 1407 - 1409 (2015/11/24)
The silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for the stereoselective synthesis of (E)-iodovinyloxazolidinones was developed. The silver-catalytic system could be applied to various propargylic amines to afford the corresponding iodovinyloxazolidinones in high yields. The structure of the oxazolidinone was confirmed by X-ray structure analysis to be the Eisomer for the geometry of the exo-olefin. The silver-catalyzed cyclization and replacement of silver with the iodine group in the intermediate were thought to be crucial steps.
