cas 17329-20-3, (1-Isocyanoethyl)benzene | Articles data

Articles about 17329-20-3Total 17 be found

Article title
Article abstract
Author
Journal number and time
Download

Concentration-dependent circularly polarized luminescence of chiral cyclometalated platinum(II) complexes for electroluminescence
Circularly polarized organic light-emitting diodes (CP-OLEDs) have been attracting increasing attention due to the direct generation of CP light, and they show the improved image contrast and luminous efficiency in OLEDs displays. In this work, a pair of chiral Pt(II) complexes with methylbenzylisocyanide and 1,3-bis(2-pyridyl)benzene as a tridentate N∧C∧N ligand were synthesized. Both of them exhibited bright green emission in dilute acetonitrile solution, while strong orange emission in high concentration of acetonitrile solution. However, when the complexes were doped into polymethyl methacrylate, the green emission originated from intrinsic single molecule can be changed to the red emission from excimer by adjusting the doping ratios. More importantly, the amplification of CPL signal can be achieved compared with the solution state. Furthermore, the monochrome devices were fabricated by utilizing these two enantiomers as emitters.
Guo, Song,Han, Jianmei,Liu, Shujuan,Lu, Hu,Tao, Peng,Xu, Yanan,Zhang, Xinwen,Zhao, Qiang,Zheng, Xiaokang
(2020)
Read Online

Method for preparing isonitrile compound
The invention discloses a method for preparing an isonitrile compound, and belongs to the field of organic synthesis. According to the method, sodium chlorodifluoroacetate or potassium bromodifluoroacetate is used as a difluoromethyl source and is condensed with primary amine under the action of alkali to obtain an isocyanide target product, so that isocyanide is generated in situ on the primary amine. The reaction raw materials, alkali and solvent used in the method are simple and easy to obtain, wide in source and convenient to operate, do not need special storage and use conditions, the method has the advantages of safety, low cost, high yield, simple process, environmental friendliness and the like, and has important application value in the fields of medicine, protein and polypeptidepreparation, pesticides, high polymer materials, dyes and the like.
-
Paragraph 0062-0067

(2021/01/30)

Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides
A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.
Leech, Matthew C.,Petti, Alessia,Tanbouza, Nour,Mastrodonato, Andrea,Goodall, Iain C. A.,Ollevier, Thierry,Dobbs, Adrian P.,Lam, Kevin
supporting information
p. 9371 - 9375
(2021/12/09)

Isocyanide 2.0
The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is
Ahmadian-Moghaddam, Maryam,D?mling, Alexander,Patil, Pravin
supporting information
p. 6902 - 6911
(2020/11/09)

Synthesis of isocyanides by reacting primary amines with difluorocarbene
A general, convenient, and friendly route for preparing a versatile building block of isocyanides from primary amines is developed. Difluorocarbene, generated in situ from decarboxylation of chlorodifluoroacetate, reacts efficiently with primary amines to produce isocyanides. Various primary amines are well tolerated, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is demonstrated, showing its practical capacity in drug design and peptide modification.
Si, Yi-Xin,Zhu, Peng-Fei,Zhang, Song-Lin
supporting information
p. 9086 - 9090
(2020/11/30)

Nonacidic Farnesoid X Receptor Modulators
As a cellular bile acid sensor, farnesoid X receptor (FXR) participates in regulation of bile acid, lipid and glucose homeostasis, and liver protection. Clinical results have validated FXR as therapeutic target in hepatic and metabolic diseases. To date, potent FXR agonists share a negatively ionizable function that might compromise their pharmacokinetic distribution and behavior. Here we report the development and characterization of a high-affinity FXR modulator not comprising an acidic residue.
Flesch, Daniel,Cheung, Sun-Yee,Schmidt, Jurema,Gabler, Matthias,Heitel, Pascal,Kramer, Jan,Kaiser, Astrid,Hartmann, Markus,Lindner, Mara,Lüddens-D?mgen, Kerstin,Heering, Jan,Lamers, Christina,Lüddens, Hartmut,Wurglics, Mario,Proschak, Ewgenij,Schubert-Zsilavecz, Manfred,Merk, Daniel
supporting information
p. 7199 - 7205
(2017/09/07)

Synthesis of 3,4-dihydroisoquinolines by cyclization of 1-bromo-2-(2-isocyanoalkyl)benzenes with butyllithium
A new and convenient method for the preparation of 3,3-disubstituted 3,4-dihydroisoquinolines has been developed. Thus, the reaction of 1-bromo-2-(bromomethyl)benzenes with (1-isocyano-1-lithioalkyl)benzenes, generated by the treatment of (1-isocyanoalkyl
Kobayashi, Kazuhiro,Matsumoto, Naoki,Matsumoto, Kota
p. 389 - 397
(2013/03/14)

Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation-reduction condensation
Cyanation of various alcohols by a new type of oxidation-reduction condensation is described. Primary alkyl diphenylphosphinites, 2,6-dimethyl-1,4-benzoquinone (DMBQ), and diethyl cyanophosphonate gave the corresponding nitriles in high yields. During the above experiment on cyanation of 4-phenylbutan-2-ol, the unexpected formation of a mixture of nitrile and isocyanide was observed. After careful examination of the reaction conditions, selective synthesis of isocyanides from secondary alcohols was successfully accomplished by the use of zinc oxide (ZnO) as an additive. Reaction of tertiary alcohols provided the corresponding isocyanides exclusively in the absence of an additive. Cyanation of optically active alcohols was tried in order to clarify the stereochemistry of this reaction, and the reaction was thus proved to proceed with the inversion of configuration.
Masutani, Kouta,Minowa, Tomofumi,Hagiwara, Yoshiaki,Mukaiyama, Teruaki
p. 1106 - 1117
(2007/10/03)

Selective synthesis of isocyanides from secondary alcohols by a new type of oxidation-reduction condensation
Selective synthesis of isocyanides from secondary alcohols via alkyl diphenylphosphinites is established by a new type of oxidation-reduction condensation in controlling the ambident reactivity of cyanide anion. In the presence of ZnO, isocyanides are obtained exclusively in moderate to high yields. Copyright
Masutani, Kouta,Minowa, Tomofumi,Mukaiyama, Teruaki
p. 1124 - 1125
(2007/10/03)

Compounds for inhibiting β-amyloid peptide release and/or its synthesis
Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis.
-
(2008/06/13)

Methods and compounds for inhibiting β-amyloid peptide release and/or its synthesis
Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.
-
(2008/06/13)

Compounds for inhibiting β-amyloid peptide release and/or its synthesis
Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis.
-
(2008/06/13)

Electrochemical synthesis of isocyanides and 1,n-diisocyanides
Some isocyanide structures have shown fungicide, antibiotic, insecticide, akarizide and other biological activities. Electrochemical reduction of substituted tosylmethylisocyanides (TosMICs) in acetonitrile/0,1 M tetraalkylammonium supporting-electrolyte at Hg-electrodes led to new alkyl-, aryl and 1,n-diisocyanides in good yields. The reaction proceeds in a two-electron C,S-cleavage, reducing exclusively the tosyl-function. The high selectivity of the corresponding ECE-mechanism is supported by quantum- chemical calculation.
Hess, Ulrich,Brosig,Komenda,Schaefer
p. 412 - 417
(2007/10/03)

Photooxygenation of 1,4-Diaza-1,3-butadienes (α-Diimines): Formation of Isonitriles
Dye-sensitized photooxygenations of cyclic and acyclic 1,4-diaza-1,3-butadienes (α-Diimines), carrying a methyl or an ethyl group in the 2-position, yield isonitriles and amides, as well as formaldehyde or acetaldehyde.Thus, cyclic α-diimines such as 5,6-dimethyl- (1a), 5-methyl-6-phenyl- (1b), 5-methyl-6-(p-tolyl)- (1c), and 5,6-diethyl-2,3-dihydropyrazine (1d) yield the respective 1-isocyano-2-(acylamino)ethanes 2a-d, whereas 5-isopropyl-6-phenyl- (1e) and 5,6-diphenyl-2,3-dihydropyrazine (1f) are inert toward photooxygenation.Acyclic α-diimines such as 1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene (4a), 2,5-diaza-3,4-dimethyl-2,4-hexadiene (4b), 1,4-diaza-2,3-dimethyl-1,4-diphenyl-1,3-butadiene (4c), and N,N'-bis-2,3-butanediimine (4d) afford the respective isonitriles 5a-d and acetamides 6a-d.With retention of configuration, chiral α-diimines such as (-)-N,N'-bis-2,3-butanediimine and its R,R enantiomer , and (3S,8S)-(-)-3,8-dicarbomethoxy-4,7-diaza-2,5,6,9-tetramethyl-4,6-decadiene yield the corresponding enantiomerically pure isonitriles (S)-5e, (R)-5e, and (S)-5f and acetamides (S)-6e, (R)-6e, and (S)-6f.Evidence for a singlet oxygen reaction is presented.A working hypothesis is proposed which includes the formation of a transient hydroperoxide 7 that fragments into an isonitrile molecule, an aldehyde, and an N-alkyl- or N-arylnitrilium cation and a hydroxide ion; the latter combine to yield the amide groups in 2a-d and the amide compounds 6a-f.
Gollnick, Klaus,Koegler, Sigrid,Maurer, Dorothee
p. 229 - 234
(2007/10/02)

Die Isocyanid-Cyanid-Umlagerung - Mechanismus und praeparative Anwendung
Bis vor kurzem war die Isocyanid-Cyanid-Umlagerung hauptsaechlich als Beispiel fuer eine unimolekular verlaufende Gasphasenreaktion bekannt und nur fuer einfache Systeme kinetisch untersucht.Kinetikstudien in Loesung wurden erst moeglich, als man eine ueberlagerte, zum gleichen Produkt fuehrende Radikalkette erkannte und diese inhibieren konnte.Die Geschwindigkeit der Isomerisierung erwies sich als kaum von der Struktur und von Substituenten abhaengig.Allenfalls starke sterische Hinderung in drei Dimensionen wie in tris-α-substituierten Triptylcylisocyaniden fuehrt zu einer deutlichen Erhoehung der Aktivierungsenthalpie.Die Ergebnisse lassen sich mit einem rein sigmatropen Mechanismus deuten und sind damit in Einklang mit Voraussagen aus ab-initio-Rechnungen.Auch praeparativ laesst sich diese Umlagerung inzwischen nutzen.Bei der Blitzpyrolyse sind die Ausbeuten an Cyanid nahezu quantitativ.Allylisocyanide reagieren ohne Allylisomerisierung und optisch aktive Isocyanide unter vollstaendiger Retention.Die Umlagerung kann sowohl Bestandteil wirtschaftlich interessanter Synthesen, z.B. der Entzuendungshemmer Ibuprofen und (S)-Naproxen, sein als auch beim Aufbau optisch aktiver β-Acyloxycyanide, die nuetzliche Synthesebausteine sind, aus optisch aktiven α-Aminosaeuren helfen.
Ruechardt, Christoph,Meier, Michael,Haaf, Klaus,Pakusch, Joachim,Wolber, Erwin K. A.,Mueller, Barbara
p. 907 - 915
(2007/10/02)

Generation of Homochiral Quaternary Carbon Centres from (Vinylketenimine)tricarbonyliron(0) Complexes
The first homochiral (vinylketenimine)tricarbonyliron(0) complexes have been formed.Nucleophilic attack occurs exclusively on their exo face and after an oxidative work-up homochiral β,γ-unsaturated carboxylic acids containing an α quaternary carbon centre are obtained.
Alcock, Nathaniel W.,Pike, Graham A.,Richards, Christopher J.,Thomas, Susan E.
p. 531 - 534
(2007/10/02)

ATROPISOMERISM IN POLYMERS. SCREW-SENSE SELECTIVE POLYMERIZATION OF ISOCYANIDES BY INHIBITING THE GROWTH OF ONE ENANTIOMER OF A RACEMIC PAIR OF HELICES.
The authors describe a method for the preparation of a polymer with an excess of either left- or right-handed helices, starting from an achiral isocyanide. To this end, they added a slowly polymerizing optically active isocyanide as comonomer to a rapidly polymerizing achiral isocyanide. CD spectra and optical rotation indicate that the screw sense of the resulting polymer samples is opposite to the one preferred by the homopolymer of the optically active comonomer. A mechanism is proposed according to which the optically active comonomer is preferentially incorporated in one of the two helices formed from the achiral isocyanide, viz. the one that corresponds to its own homopolymer.
Kamer,Cleij,Nolte,Harada,Hezemans,Drenth
p. 1581 - 1587
(2007/10/02)