56564-44-4Relevant academic research and scientific papers
New half-sandwich (η6-p-cymene)ruthenium(II) complexes with benzothiazole hydrazone Schiff base ligand: Synthesis, structural characterization and catalysis in transamidation of carboxamide with primary amines
Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
supporting information, (2020/10/18)
Few half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by benzothiazole hydrazone Schiff bases were synthesized. The new complexes possess the general formulae [Ru(η6-p-cymene)(L)Cl] (1-3) (L = salicyl((2-(benzothiazol-2-yl)hydrazono)methylphenol) (SAL-HBT), 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT) or naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methyl phenol) (NAP-HBT). All compounds were fully studied by analytical, spectroscopic techniques (IR, NMR) and also by mass spectrometry. The solid state structure of the complex 3 reveals the coordination of p-cymene moieties with ruthenium(II) in a three-legged piano-stool geometry along with benzothiazole hydrazone Schiff base ligand in a monobasic bidentate fashion. The catalytic properties of the complexes were screened in transamidation of primary amide with amines after optimization with respect to solvent, substituents, time and catalyst loading. The results show that the complex 3 is the most efficient catalyst for the transamidation of carboxamides with amines.
Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: Direct access to biaryls
Tang, Ren-Jin,He, Qing,Yang, Luo
supporting information, p. 5925 - 5928 (2015/03/30)
A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis.
CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
supporting information, p. 599 - 601 (2015/02/19)
CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
Complexes of silicon and phosphorus chlorides with nitrogen-containing bases as the condensing agents in the synthesis of amides
Besgubenko, L. V.,Pipko, S. E.,Sinitsa, A. D.
supporting information, p. 1382 - 1390,9 (2020/09/16)
High effectiveness of new condensing agents on the basis of complexes of silicon and phosphorus chlorides with nitrogen-containing bases in the synthesis of amides from carboxylic acids and amines and also in heterocyclization is shown. Factors affecting the readiness of formation of the amide bond and the yields of the final products are established.
Facile synthesis of thiazoles via an intramolecular thia-Michael strategy
Sasmal, Pradip K.,Sridhar,Iqbal, Javed
, p. 8661 - 8665 (2007/10/03)
A mild and efficient method for the synthesis of substituted thiazoles is reported via one-pot N-desilylation, thioacylation/oxythioacylation/thiothioacylation followed by thia-Michael cycloisomerisation. This method has a general applicability to introdu
Addition of organostannanes to isocyanate catalyzed by a rhodium complex
Koike, Tooru,Takahashi, Masabumi,Arai, Nobumichi,Mori, Atsunori
, p. 1364 - 1365 (2007/10/03)
Arylstannanes add to isocyanate in the presence of a rhodium catalyst to afford amides in good to excellent yields. Use of a phenol derivative as an additive is found to play an essential role for the successful reaction.
Reaction of N-Aryl- and N-Alkyl-benzimidoyl Chlorides with Silver Nitrate
Iley, Jim,Carvalho, Emilia,Norberto, Fatima,Rosa, Eduarda
, p. 281 - 290 (2007/10/02)
N-Arylbenzimidoyl chlorides, in which the N-aryl group is unsubstituted at the ortho- and para-positions, react with AgNO3 to yield N-(nitroaryl)benzamides, in which the NO2 group resides in the ortho- or para-position.N-Arylbenzimidoyl chlorides, in which the N-aryl ring is 2,4,6-trisubstituted, react with AgNO3 to yield the corresponding N-aryl-N-nitrobenzamides.The formation of both types of product can be explained by the intermediacy of an O-nitro imidate.Spectroscopic and chemical evidence is presented for the formation of this intermediate in the reaction of N-(2,4,6-trisubstituted phenyl)benzimidoyl chlorides with AgNO3.Rearrangement of the O-nitro imidate is unimolecular and intramolecular.The rate of rearrangement is independent of the substituent in the C-aryl ring, but increases with the electon-withdrawing ability of the substituents in the N-aryl ring.A mechanism is proposed in which the imidoyl chloride reacts with AgNO3 to produce first a nitrilium ion which goes on to form an O-nitro imidate that subsequently rearranges via a homolytic cleavage of the O-NO2 bond.The ortho:para ratios of N-(nitroaryl)benzamides obtained in the present work indicate that O-nitro imidates are not responsible for the high 1/2ortho:para ratios sometimes observed in the nitration of anilides.N-Alkylbenzimidoyl chlorides react with AgNO3 to form the corresponding N-nitro- and N-nitrosobenzamides.The mechanism of formation of the N-alkyl-N-nitrobenzamide arises from a pathway analogous to that for N-aryl-N-nitrobenzamides, involving a nitrilium ion that gives rise to an O-nitro imidate.The evidence for the formation of the N-nitrosobenzamide points to an alternative reaction of the imidoyl chloride with AgNO3.One possible mechanism for this reaction is described.
Rearrangement of Imidoyl Nitrates to N-Nitro Amides: an Intramolecular O-to-N Migration of a Nitro Group
Carvalho, Emilia,Iley, Jim,Rosa, Eduarda
, p. 1249 - 1250 (2007/10/02)
Imidoyl nitrates, formed by the reaction of imidoyl chlorides with AgNO3, rearrange via a unimolecular, intramolecular mechanism probably involving homolytic fission of the O-N bond to yield N-nitro amides; migration of the nitro group in N-arylimidoyl nitrates to the ortho- and para-positions of the N-aryl ring does not involve a special ortho-directing effect.
