3154-51-6Relevant articles and documents
Environmentally benign process for the synthesis of N-formyl amino acid esters
Kotha, Sambasivarao,Behera, Manoranjan,Khedkar, Priti
, p. 7589 - 7590 (2004)
Several amino acid ester hydrochlorides were reacted with ammonium formate to give N-formyl amino acid esters in good yields.
Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates
Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei
supporting information, p. 5417 - 5421 (2021/09/29)
The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).
Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas
Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng
supporting information, p. 648 - 652 (2020/12/21)
Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.
Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability
Novotortsev, Vladimir K.,Kukushkin, Maxim E.,Tafeenko, Viktor A.,Skvortsov, Dmitry A.,Kalinina, Marina A.,Timoshenko, Roman V.,Chmelyuk, Nelly S.,Vasilyeva, Liliya A.,Tarasevich, Boris N.,Gorelkin, Petr V.,Erofeev, Alexander S.,Majouga, Alexander G.,Zyk, Nikolai V.,Beloglazkina, Elena K.
, p. 1 - 26 (2021/03/09)
A regio-and diastereoselective synthesis of two types of dispiro derivatives of 2-selenoxoim-idazolidin-4-ones, differing in the position of the nitrogen atom in the central pyrrolidine ring of the spiro-fused system—namely, 2-selenoxodispiro[imidazolidine-4,3′-pyrrolidine-2′,3′′-indoline]-2′′, 5-diones (5a-h) and 2-senenoxodispiro[imidazolidine-4,3′-pyrrolidine-4′,3′′-indoline]-2′′,5-diones (6a-m)—were developed based on a 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or formaldehyde and sarcosine to 5-arylidene or 5-indolidene-2-selenoxo-tetrahydro-4H-imidazole-4-ones. Selenium-containing dispiro indolinones generally exhibit cytotoxic activity near to the activity of the corresponding oxygen and sulfur-containing derivatives. Compounds 5b, 5c, and 5e demonstrated considerable in vitro cytotoxicity in the 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyl tetrazolium bromide (MTT) test (concentration of compounds that caused 50% death of cells (CC50) 7.6–8.7 μM) against the A549 cancer cell line with the VA13/A549 selectivity index 5.2– 6.9 and compound 6e—against the MCF7 cancer cell line (CC50 20.6 μM, HEK293T/A549 selectivity index 1.6); some compounds (5 and 6) increased the level of intracellular reactive oxygen species (ROS) in the experiment on A549 and PC3 cells using platinized carbon nanoelectrode. The tests for p53 activation for compounds 5 and 6 on the transcriptional reporter suggest that the investigated compounds can only have an indirect p53-dependent mechanism of action. For the compounds 5b, 6b, and 6l, the ROS generation may be one of the significant mechanisms of their cytotoxic action.
ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS
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Paragraph 0297, (2021/10/22)
The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.
Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
supporting information, p. 5726 - 5733 (2020/08/21)
N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
Influence of the C-terminal substituent on the crystal-state conformation of Adm peptides
Mir, Fatemeh M.,Crisma, Marco,Toniolo, Claudio,Lubell, William D.
, (2020/03/11)
The bis-functionalized diamondoid α-amino acid 2-aminoadamantane-2-carboxylic acid (Adm) has been used as the building block of four Nα-formyl homo-dipeptide alkylamide sequences via a solution-phase Ugi multicomponent reaction approach. The conformers of these peptides have been determined in the crystalline state by X-ray diffraction to distinguish the influences of the C-terminal substituent. One of the Adm peptides folds into an open and a hydrogen-bonded γ-turn geometry. Moreover, 3D-structures have been observed featuring two consecutive γ-turns in an incipient γ-helical structure, a significantly distorted nonhelical β-turn, as well as an S-shaped conformation with opposite helical screw senses. A significant topological variety is thus exhibited by the -Adm-Adm- sequences contingent on their C-terminal substituents, illustrating both the broad conformational potential and the need for further characterization of this sterically bulky residue in explorations of its ?, ψ space.
One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction
Attorresi, Cecilia I.,Bonifazi, Evelyn L.,Ramírez, Javier A.,Gola, Gabriel F.
supporting information, p. 8944 - 8949 (2018/12/10)
A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway.
Tetraethylorthosilicate as a mild dehydrating reagent for the synthesis of N-formamides with formic acid
Nishikawa, Yasuhiro,Nakamura, Hidetsugu,Ukai, Norimitsu,Adachi, Wakana,Hara, Osamu
supporting information, p. 860 - 863 (2017/02/10)
The synthesis of N-formamides with formic acid as a formyl source under mild conditions was achieved using tetraethylorthosilicate (TEOS), a low cost and environmentally benign reagent. The mild conditions in this system enable the formylation of a variety of amino acid derivatives including stereochemically labile phenylglycine ethyl ester with 96% ee. This new protocol could also be applied to simple amines including weakly basic aniline derivatives, giving various primary and secondary formamides.
PROCESSES FOR THE PREPARATION OF DIASTEREOMERICALLY AND ENANTIOMERICALLY ENRICHED OXAZOLINES
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Page/Page column 22-23, (2017/05/28)
The invention relates to an industrially viable and advantageous process for the preparation of (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid, having the following formula (I) generally known as Droxidopa, or of intermediates useful in the synthesis thereof.
