34918-76-8Relevant academic research and scientific papers
N-alkylation of α-iminophosphonates and application to Horner-Wadsworth-Emmons reaction
Shimizu, Makoto,Tateishi, Masasato,Mizota, Isao
, p. 1752 - 1754 (2014)
N-Alkylation of α-iminophosphonates with Grignard reagents gives α-N-alkylaminophosphonates. A subsequent Horner-Wadsworth-Emmons reaction of the intermediary α-metalated phosphonate takes place with aldehydes to give enamines. The enamine thus prepared reacts with MVK to give a four-component coupling product.
Studies towards the design and synthesis of novel 1,5-diaryl-1h-imidazole-4-carboxylic acids and 1,5-diaryl-1h-imidazole-4-carbohydrazides as host ledgf/p75 and hiv-1 integrase interaction inhibitors
Bode, Moira L.,Fish, Muhammad Q.,Mabel Coyanis, E.,Rashamuse, Thompho J.
, (2021/10/25)
Two targeted sets of novel 1,5-diaryl-1H-imidazole-4-carboxylic acids 10 and carbohy-drazides 11 were designed and synthesized from their corresponding ester intermediates 17, which were prepared via cycloaddition of ethyl isocyanoacetate 16 and diarylimi
Synthesis of Imidoyl Chlorides Using Phosphorus Trichloride
Nguyen, T. L.,Popov, Yu. V.,Shishkin, E. V.,Shishkin, V. E.,Vo, T. L. Q.,Zotov, Yu. L.
, p. 849 - 851 (2021/06/12)
Abstract: The reaction of carboxamides with phosphorus trichloride under heating at 75–80°C for 1 h in the presence of a 4-dimethylaminopyridine catalyst was used to synthesize imidoyl chlorides in yields of 63–99%.
Synthesis of Nitrogen-Containing Polyaromatics by Aza-Annulative π-Extension of Unfunctionalized Aromatics
Itami, Kenichiro,Ito, Hideto,Kawahara, Kou P.,Matsuoka, Wataru
supporting information, p. 6383 - 6388 (2020/03/13)
Nitrogen-containing polycyclic aromatic compounds (N-PACs) are an important class of compounds in materials science. Reported here is a new aza-annulative π-extension (aza-APEX) reaction that allows rapid access to a range of N-PACs in 11–84 % yields from readily available unfunctionalized aromatics and imidoyl chlorides. In the presence of silver hexafluorophosphate, arenes and imidoyl chlorides couple in a regioselective fashion. The follow-up oxidative treatment with p-chloranil affords structurally diverse N-PACs, which are very difficult to synthesize. DFT calculations reveal that the aza-APEX reaction proceeds through the formal [4+2] cycloaddition of an arene and an in situ generated diarylnitrilium salt, with sequential aromatizations having relatively low activation energies. Transformation of N-PACs into nitrogen-doped nanographenes and their photophysical properties are also described.
α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
, p. 7433 - 7445 (2020/06/27)
Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with Sulfoxonium Ylides: Synthesis of 3-Aminofurans and 4-Aminoquinolines
Liang, Yong-Xin,Yang, Ming,He, Bo-Wen,Zhao, Yu-Long
supporting information, p. 7640 - 7644 (2020/10/09)
A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This reaction provides a new and efficient method for the construction of highly functionalized 3-aminofurans and 4-aminoquinolines from readily available starting materials in a single step.
Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
Cheung, Wing,Patch, Raymond J.,Player, Mark R.
supporting information, p. 2368 - 2371 (2018/05/25)
A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.
Proton-Transfer Polymerization by N-Heterocyclic Carbenes: Monomer and Catalyst Scopes and Mechanism for Converting Dimethacrylates into Unsaturated Polyesters
Hong, Miao,Tang, Xiaoyan,Falivene, Laura,Caporaso, Lucia,Cavallo, Luigi,Chen, Eugene Y.-X.
supporting information, p. 2021 - 2035 (2016/03/01)
This contribution presents a full account of experimental and theoretical/computational investigations into the N-heterocyclic carbene (NHC)-catalyzed proton-transfer polymerization (HTP) that converts common dimethacrylates (DMAs) containing no protic gr
Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines
Lin, Jian-Ping,Zhang, Feng-Hua,Long, Ya-Qiu
supporting information, p. 2822 - 2825 (2014/06/23)
A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.
Synthesis of chlorinated bicyclic C-fused tetrahydrofuro[3,2- c ]azetidin-2-ones
Ram, Ram N.,Kumar, Neeraj,Singh, Nem
supporting information; experimental part, p. 7408 - 7411 (2011/02/22)
Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-
