78558-73-3Relevant academic research and scientific papers
Photoreactive fused aziridinylpiperazines on the background of 4-substituted chalcones and their benzimidazolic analogs
Kotlyar, Volodymyr M.,Kolomoitsev, Oleksii O.,Nikolaievskyi, Dmytro V.,Pedan, Polina I.,Chumak, Andrii Yu,Orlov, Valery D.,Shishkina, Svitlana V.,Doroshenko, Andrey O.
, p. 741 - 746 (2019/01/10)
The reaction of bromo-substituted chalcones with various diamino-compounds leads to the fused heterocyclic products, aziridinylpiperazines, exhibiting photoreactivity in the crystalline state. Crystals of 4-nitrosubstituted compounds of this family change their color from yellowish to deep violet-blue, 4-cyanosubstituted ones – from yellowish to pink at UV irradiation. Discussion on the mechanism of this phototransformation is still in progress, however, several facts points to the free radial nature of the photogenerated colored semi-products stabilized only by crystalline state of the irradiated samples. Formation of a mixture of positional isomers at interaction of bromo-chalcones with asymmetric diamines of aliphatic/alicyclic or aromatic series at synthesis of the title compounds is of significant interest as well.
Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
Kang, Ki-Tae,Park, Sang Hyun,Ryu, Do Hyun
supporting information, p. 6679 - 6683 (2019/09/12)
Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi
Verkade's Superbase as an Organocatalyst for the Strecker Reaction
Yang, Jian,Chatelet, Bastien,Ziarelli, Fabio,Dufaud, Véronique,Hérault, Damien,Martinez, Alexandre
, p. 6328 - 6332 (2018/11/23)
Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low
Lanthanide coordination polymer constructed from 2,2′-bipyridyl-4,4′-dicarboxylic acid: Structure, catalysis and fluorescence
Wang, Shengyan,Xu, Jianing,Zheng, Jifu,Chen, Xiaodong,Shan, Liang,Gao, Lijuan,Wang, Li,Yu, Miao,Fan, Yong
, p. 81 - 86 (2015/09/15)
Two new isostructural lanthanide coordination polymers (Ln-CPs) [Ln2(bpdc)3(DMF)2] (Ln = Tb for 1, Eu for 2) with two kinds of one-dimensional channels along the a axis, were synthesized by 2,2′-bipyridyl-4,4′-dicarboxylic acid (H2bpdc) under solvothermal conditions. With exposed Lewis acid Ln3+ centers, 1 as a heterogeneous catalyst shows good catalytic reactivity and selectivity for the Strecker reaction affording medium to excellent conversion yields. Luminescent studies illustrate that 1 and 2 show intensive green and red luminescence triggered by efficient antenna effect of ligands under UV light, respectively. Moreover, 1 exhibits sensitive fluorescent response to Cu2+ in DMF solution.
Synthetic application of in situ generation of N-acyliminium ions from α-amido p-tolylsulfones for the synthesis of α-amino nitriles
Kadam, Santosh T.,Thirupathi, Ponnaboina,Kim, Sung Soo
experimental part, p. 1684 - 1688 (2010/04/04)
In the presence of catalytic amount of bismuth bromide (5 mol %) the α-amido p-tolylsulfones are converted into N-acyliminium ions, which undergo the nucleophilic addition of trimethylsilyl cyanide (TMSCN) to provide the N-protected α-amino nitriles in very good yield. A variety of α-amido p-tolylsulfones were prepared from aromatic as well as aliphatic aldehydes for the synthesis of α-amino nitriles.
Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex
Abell, Joshua P.,Yamamoto, Hisashi
supporting information; experimental part, p. 15118 - 15119 (2010/01/15)
(Chemical Equation Presented) An aluminum complex was found to be high yielding and enantioselective for the addition of cyanide to aldimines and ketimines. Although catalytic asymmetric addition of cyanide to imines to generate ?-amino-protected nitriles (the Strecker reaction) has been extensively studied in the past, alternative, easier-to-handle reagents for this process are required for modern organic synthesis. To date, there are a limited number of reports utilizing alternative sources of cyanide other than KCN/HCN or TMSCN for this important reaction. The present catalyst provides uniformly high enantioselectivity for aromatic, heteroaromatic, and aliphatic aldimines and ketimines using ethyl cyanoformate as the cyanide source.
Synthesis of α-amino nitriles through Strecker reaction of aldimines and ketoimines by using nanocrystalline magnesium oxide
Kantam, M. Lakshmi,Mahendar, Koosam,Sreedhar, Bojja,Choudary
, p. 3351 - 3360 (2008/09/19)
Strecker reactions of various aldimines as well as ketoimines with TMSCN proceeded smoothly under mild conditions to give the corresponding α-amino nitriles and α,α-disubstituted α-amino nitriles, respectively, in good to excellent yields in the presence
Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure
Yan, Shunqi,Larson, Gary,Wu, Jim Z.,Appleby, Todd,Ding, Yili,Hamatake, Robert,Hong, Zhi,Yao, Nanhua
, p. 63 - 67 (2007/10/03)
Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2 A, and confirmed the design.
Strecker reaction of aldimines catalyzed by a nucleophilic N-heterocyclic carbene
Fukuda, Yoshimasa,Maeda, Yuka,Kondo, Kazuhiro,Aoyama, Toyohiko
, p. 1937 - 1939 (2007/10/03)
The first method for Strecker reaction (cyanation of imines) of aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and t-BuOK, as a nucleophilic catalyst, is described. Georg Thi
Electrophilic amination of enolates with oxaziridines: Effects of oxaziridine structure and reaction conditions
Armstrong, Alan,Edmonds, Ian D.,Swarbrick, Martin E.,Treweeke, Nigel R.
, p. 8423 - 8442 (2007/10/03)
A range of N-alkoxycarbonyl- and N-carboxamido-oxaziridines has been prepared to test the effects of oxaziridine structure on yields of enolate amination product. Side-products arising from reaction of aldehyde-derived oxaziridines with base were identified, while a ketone-derived oxaziridine afforded moderate yields of amination product with stabilised carbanions.
