2258-42-6Relevant articles and documents
Synthesis of benzannulated N-heterocyclic carbene ligands by a template synthesis from 2-nitrophenyl isocyanide
Hahn, F. Ekkehardt,Plumed, Cesar Garcia,Muender, Marco,Luegger, Thomas
, p. 6285 - 6293 (2004)
The reaction of 2-nitrophenyl isocyanide 2 with [M(CO)5(thf)] (M = Cr, Mo, W) yields the isocyanide complexes [M(CO)5(2)] (3: M = Cr; 4: M = Mo; 5: M = W). Complexes 3-5 react with elemental tin under reduction of the nitro function of the isocyanide ligand to give the complexes with the unstable 2-aminophenyl isocyanide ligand. The coordinated 2-aminophenyl isocyanide ligand in all three complexes reacts spontaneously under intramolecular nucleophilic attack of the primary amine at the isocyanide carbon atom to yield the complexes with the NH,NH-benzimidazol-2-ylidene ligand (6: M = Cr; 7: M = Mo; 8: M = W). An incomplete reduction of the nitro group in 3-5 is observed when hydrazine hydrate is used instead of tin. Here the formation of complexes with a coordinated 2-hydroxylamine-functionalized phenyl isocyanide [(CO)5M-CN-C6H4--2-N(H)-OH] is postulated and this unstable ligand again undergoes intramolecular cyclization to give the NH,NOH-stabilized benzimidazol-2-ylidene complexes 9-11. The tungsten derivative 11 can be allylated stepwise by a deprotonation/ alkylation sequence first at the OH and then at the NH position to yield the monoallylated and diallylated species 12 and 13. The molecular structures of 3-5 and 12-13 were established by X-ray crystallography.
Total synthesis of (±)-welwitindolinone A isonitrile
Reisman, Sarah E.,Ready, Joseph M.,Hasuoka, Atsushi,Smith, Catherine J.,Wood, John L.
, p. 1448 - 1449 (2006)
A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol. Copyright
Linear 6,6′-biazulenyl framework featuring isocyanide termini: Synthesis, structure, redox behavior, complexation, and self-assembly on Au(111)
Maher, Tiffany R.,Spaeth, Andrew D.,Neal, Brad M.,Berrie, Cindy L.,Thompson, Ward H.,Day, Victor W.,Barybin, Mikhail V.
, p. 15924 - 15926 (2010)
The key step in accessing the title species (5), the first nonbenzenoid diisocyanobiaryl, involved an unexpected homocoupling of a 6-bromoazulene derivative. The reversible 2e- reduction of 5 was addressed electrochemically and computationally. The shifts in energies of the S 0→S1 and S0→S2 transitions for a series of related 6,6′-biazulenyl derivatives correlate with the e--donating/-withdrawing strength of their 2,2′-substituents but follow opposite trends. Species 5 adsorbs end-on (η1) to the Au(111) surface via one of its -NC groups to form a 2-nm-thick film. In addition, bimetallic coordination of 5's -NC termini can be readily achieved.
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Dunbar,Garven
, p. 4161 (1955)
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Reactions of OH and Cl with isopropyl formate, isobutyl formate, n-propyl isobutyrate and isopropyl isobutyrate
Zhang,Liang,Jiang,Cazaunau,Da?le,Mu,Mellouki
, p. 68 - 74 (2014)
The rate coefficients for the reactions of OH with isopropyl formate, isobutyl formate, n-propyl isobutyrate and isopropyl isobutyrate have been determined using both absolute and relative methods. The relative rate method has been also used to measure the room temperature rate coefficient for the reaction of Cl with the same esters. In addition, a series of runs conducted on the OH-initiated oxidation of isopropyl formate, isobutyl formate and n-propyl isobutyrate showed the formation of acetone from the three reactions. The formation of propanal was also observed for n-propyl isobutyrate.
Coordination-Driven Self-Assembly of Cyclometalated Iridium Squares Using Linear Aromatic Diisocyanides
Olumba, Morris E.,Na, Hanah,Friedman, Alan E.,Teets, Thomas S.
, p. 5898 - 5907 (2021)
Here, we demonstrate facile [4 + 4] coordination-driven self-assembly of cyclometalated iridium(III) using linear aryldiisocyanide bridging ligands (BLs). A family of nine new [Ir(C^N)2(μ-BL)]44+ coordination cages is described, where C^N is the cyclometa
Synthesis of Spiro Heterocyclic Nitroxides Derived from 4-Piperidone
Keana, John F. W.,Prabhu, Vaikunth S.,Shen, DeKang
, p. 2365 - 2367 (1988)
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Synthesis of 5-halogeno-6-amino-2'-deoxyuridines and their analogs as potential inhibitors of thymidine phosphorylase
Pan, Bai-Chuan,Chen, Zhi-Hao,Chu, Edward,Chu, Ming-Yu Wang,Chu, Shih-Hsi
, p. 2367 - 2382 (1998)
5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'- deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6- amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 μM and 6.5 μM, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.
Synthesis of dehydro-oogoniol, a female-activating hormone of Achlya: The progesterone route
McMorris,Le,Preus,Schow,Weihe
, p. 345 - 361 (1989)
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Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid
Fan, Chao,Hou, Jing,Chen, Yu-Jia,Ding, Kui-Ling,Zhou, Qi-Lin
supporting information, p. 2074 - 2077 (2021/04/05)
A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.
