10349-38-9Relevant articles and documents
Isonitriles as source and fate of imidoyl radicals: A novel homolytic α-fragmentation
Nanni, Daniele,Pareschi, Patrizia,Tundo, Antonio
, p. 9337 - 9340 (1996)
Imidoyl radicals 4a-c react with phenylacetylene to give annulation products and nitrile 12, arising from β-scission of the intermediate iminyl radical that is involved in the rearrangement of azaspirocyclohexadienyl 8. In contrast, imidoyls 4d and 15 do not react with the alkyne and give good yields of the corresponding isonitriles through a novel example of homolytic α-fragmentation.
Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study
Caltagirone, Claudia,Ciancaleoni, Gianluca,Lippolis, Vito,Mocci, Rita,Picci, Giacomo,Zielińska-B?ajet, Mariola
, p. 1389 - 1395 (2020)
The anion binding ability of a family of bis-selenoureas L1-L3 obtained by the reaction of 1,3-bis(aminomethyl)-benzene and phenylisoselenocyanate, p-methoxyphenylisoselenocyanate and naphtylisoselenocyanate, for L1, L2, and L3, respectively, has been tested and compared to that of previously described bis-urea analogues. Results suggest that the introduction of selenium leads to an increase in the acidity of the urea NH hydrogen atoms, and therefore to a stronger affinity (more than three-fold higher) towards anion species, in particular dihydrogen phosphate, in DMSO-d6. Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results.
Novel hexakis(areneisonitrile)technetium(I) complexes as radioligands targeted to the multidrug resistance P-glycoprotein
Herman,Sharma,Kronauge,Barbarics,Herman,Piwnica- Worms
, p. 2955 - 2963 (1995)
Transport substrates and modulators of the human multidrug resistance (MDR1) P-glycoprotein (Pgp) are generally lipophilic cationic compounds, many with substituted aryl moieties. We sought to synthesize aromatic technetium isonitrile complexes to enable
Synthesis of isonitriles from N-substituted formamides using triphenylphosphine and iodine
Wang, Xia,Wang, Qing-Gang,Luo, Qun-Li
, p. 49 - 54 (2015)
Treatment of N-substituted formamides with the reagent combination of triphenylphosphine and molecular iodine, in the presence of a tertiary amine, quickly produces the corresponding isocyanides in high yields under ambient conditions. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of various alkyl and aryl isocyanides.
Synthesis and cation-binding studies of gold(i) complexes bearing oligoether isocyanide ligands with ester and amide as linkers
Hau, Franky Ka-Wah,Yam, Vivian Wing-Wah
, p. 300 - 306 (2015)
A series of dinuclear gold(i) isocyanide complexes of bis(alkynyl)calix[4]arene was designed and synthesized, and their photophysical and cation recognition properties were studied. Complex 1, [{calix[4]arene-(OCH2CONH-C6H4CC)2}{Au(CN-C6H4O(CH2CH2O)2CH3)}2], was found to show a high selectivity towards Al3+ in CH2Cl2-MeCN (1-1 v/v). Upon addition of Al3+, drastic changes in the electronic absorption, emission and 1H NMR spectra were observed. These changes have been attributed to the formation of Au(i)?Au(i) interactions induced by the high binding affinity of the amide site for the Al3+ ion, instead of the high binding affinity expected of the oligoether site for alkali and alkaline earth metal ions. Further studies with the control complex, [{calix[4]arene-(OOC-C6H4CC)2}{Au(CN-C6H4O(CH2CH2O)2CH3)}2] (4), indicated that the amide carbonyl oxygen in the flexible pendants is crucial for the binding of Al3+. The Royal Society of Chemistry 2016.
Thermal oligomerisation of aryl isocyanides: Formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines
Boeyens, Jan C.A.,Cook, Leanne M.,Ding, Yunxiang,Fernandes, Manuel A.,Reid, David H.
, p. 2168 - 2172 (2003)
The aryl isocyanides 1-4 are converted at 150°C into the hexameric pyrazino[1,2-a:4,5-a′]diindoles 15-19. 4-Fluorophenyl isocyanide, when heated at 135°C, gave the hexamer 19 and the tetrameric indigo di-arylimine 9, and when kept at ambient temperature g
Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines
Yuan, Yao,Dong, Wu-Heng,Gao, Xiao-Shuang,Xie, Xiao-Min,Zhang, Zhao-Guo
, p. 11900 - 11903 (2019)
A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.
Development of an Industrial Process Based on the Groebke-Blackburn-Bienaymé Multicomponent Reaction: Efficient Preparation- of 3-Aminoimidazo[1,2-a]pyrazines
Baenziger, Markus,Durantie, Estelle,Mathes, Christian
, p. 2266 - 2274 (2017)
3-Aminoimidazo[1,2-a]pyrazine is an important scaffold that is found in many drugs. This scaffold is rapidly accessible through a Groebke-Blackburn-Bienaymé cyclisation starting from an aminopyrazine, an aldehyde and an isocyanide. A scale-up process of this multicomponent reaction has been achieved in high yield and with excellent purity. The scope and limitations of this process leading to various 3-aminoimidazo[1,2-a]pyrazines are disclosed.
Access to Unsymmetrically Substituted Diaryl Gold N-Acyclic Carbene (NAC) and N-Heterocyclic Carbene (NHC) Complexes via the Isonitrile Route
Vethacke, Vanessa,Claus, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Meister, Arne,Huber, Jonas F.,Paschai Darian, Leon K.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 536 - 554 (2021/10/20)
A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes was synthesized via the isonitrile route by three different methods: (a) solvent free in a melt, (b) mechanochemically and (c) in THF at room temperature. The latter method can also be used to synthesize unsaturated gold NHC complexes. These methods overall offer access to a broad array of new complexes and remove one of the previous limitations of the isonitrile route to NAC and NHC complexes of gold, namely the inability to react with the less nucleophilic aromatic amines. The new complexes also proved to be successful as pre-catalysts in the gold-catalyzed phenol synthesis. (Figure presented.).
Synthesis of isocyanides by reacting primary amines with difluorocarbene
Si, Yi-Xin,Zhu, Peng-Fei,Zhang, Song-Lin
supporting information, p. 9086 - 9090 (2020/11/30)
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.
