69044-00-4Relevant academic research and scientific papers
Photolytic amino etherification reactions of aryl diazoacetates with N-heterocycles and a stoichiometric amount of dioxane/tetrahydropyran in aqueous medium: Synthesis of 1,4-dioxepane/1,4,7-dioxazonan-6-one systems
Das, Ranajit,Maiti, Debajit,Sen, Subhabrata
supporting information, p. 8533 - 8544 (2021/11/17)
Herein we have reported a blue LED mediated reaction of aryl diazoacetate with a stoichiometric amount of 1,4-dioxane/tetrahydropyran (THP) and various heterocycles like indoles, pyrroles, phthalimides, thiazolidinediones and hydantoins in water. During the reaction, various aryl diazoacetates were converted to oxonium ylides by reacting with 1,4-dioxane and THP. These ylides generated in aqueous medium (under metal- and base-free conditions) were then used for the amino etherification of the aforementioned heterocycles in excellent yield. The ylides underwent a [1,2] shift to afford substituted 1,4-dioxepanes. Phthalimide products were also converted to 1,4,7-dioxazonan-6-ones. Reaction kinetics, Hammett's plot and DFT calculations (solvent phase) rationalize the ylide formation and subsequent reactions with the nucleophiles. The reaction was also demonstrated at the multigram scale. This amino etherification reaction of aryl diazoacetates in aqueous medium demonstrated a sustainable process of converting toxic 1,4-dioxane in functionalizing heterocycles. This journal is
Blue light-promoted N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives
Okada, Celso Y.,dos Santos, Caio Y.,Jurberg, Igor D.
supporting information, (2020/07/03)
A photochemical protocol using blue light allows the N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates to afford the corresponding α-amino esters. This method is experimentally simple, inexpensive and tolerates numerous functional groups, thus allowing the straightforward preparation of a variety of α-aryl amino acid derivatives in good yields.
PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
, p. 1180 - 1185 (2019/01/26)
A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
Synthesis of novel isoindolone derivatives via cascade reactions. Contrasting diastereoselectivity under solution-phase vis-a-vis solvent-free ball-milling reaction conditions
Sánchez-Antonio, Omar,González-Olvera, Rodrigo,Aguilera-Cruz, Alejandro,Reyes-Ramírez, Adelfo,Juaristi, Eusebio
, (2019/10/14)
The highly diastereoselective synthesis, crystallographic analysis, and full characterization of several novel heterocycle-fused isoindolones is described. The synthetic strategy involves a cascade Michael/aldol-like cyclization reaction between N-substituted phthalimides rac-1 or 2 and several α,β-unsaturated electrophiles to afford the tricyclic systems pyrrolo[2,1- a]isoindolone and tetrahydropyrido[2,1-a]isoindolone. This synthetic strategy offers a convenient alternative to existing procedures for the preparation of isoindolone derivatives fused to five- and six-membered rings. X-ray crystallographic analysis allowed the determination of relative configurations and revealed that the synthesized compounds exhibit significant structural distortion, especially in the five membered rings. Relevantly, the diastereomeric distribution of products depends substantially on whether the cascade reaction is carried out under solution vis-a-vis solvent-free conditions.
The Rh(II)-catalyzed formal N-S bond insertion reaction of aryldiazoacetates into: N -phenyl-sulfenyl phthalimide
Song, Zhuang,Wu, Yizhou,Xin, Tao,Jin, Chao,Wen, Xiaoan,Sun, Hongbin,Xu, Qing-Long
, p. 6079 - 6082 (2016/05/19)
The Rh(ii)-catalyzed sulfur ylide [1,2]-rearrangement of carbenoids generated from aryldiazoacetates has been realized via N-S bond insertion, generating tertiary sulfides in moderate to excellent yields. This demonstrates the first use of the sulfur ylide [1,2]-rearrangement undergoing N-S bond insertion. This protocol could proceed smoothly with high regioselectivity, low catalyst loading (0.1 mol% Rh2(OAc)4), gram-scale reaction and broad substrate scope. And the product could be converted into glycine derivatives through simple procedures.
Design of reaction media for nucleophilic substitution reactions by using a catalytic amount of an amphiphilic imidazolium salt in water
Asano, Keisuke,Matsubara, Seijiro
experimental part, p. 989 - 1002 (2010/10/19)
Molecules of an amphiphilic imidazolium salt assemble in water to form a hydrophobic membrane including an interface consisting of ammonium species. Such an interface works as a reaction medium like an ionic liquid. We used the medium for nucleophilic substitution reactions between alkyl halides and anionic nucleophiles. This procedure allowed the reactions to proceed efficiently in water without any organic solvent.
Palladium-catalysed asymmetric allylic substitution: Synthesis of α- and β-amino acids
Bower, Justin F.,Jumnah, Roshan,Williams, Andrew C.,Williams, Jonathan M. J.
, p. 1411 - 1420 (2007/10/03)
Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.
