7549-96-4Relevant academic research and scientific papers
Novel synthesis of 1-substituted-4-imidazolecarboxylates via solvent-free cycloaddition reaction between formamidines and isocyanides
Cao, Han,Bie, Fu-sheng,Liu, Xue-jing,Han, Ying,Ma, Jie,Shi, Yi-jun,Yan, Peng,Sun, Chao-yue,Wang, Hai-meng
, (2020/04/27)
A simple and efficient protocol for cyclization between formamidines and ethyl isocyanoacetate has been described in the absence of metal catalyst and solvent. A series of 1-substituted-4-imidazolecarboxylates were synthesized in moderate to good yields with DABCO as base additive.
Oxo/Imido heterometathesis reactions catalyzed by a silica-supported tantalum imido complex
Zhizhko, Pavel A.,Zhizhin, Anton A.,Belyakova, Olga A.,Zubavichus, Yan V.,Kolyagin, Yuriy G.,Zarubin, Dmitry N.,Ustynyuk, Nikolai A.
, p. 3611 - 3617 (2013/07/26)
Grafting Ta(=NtBu)(CH2CMe2Ph)3 onto the surface of silica partially dehydroxylated at 300°C leads to the formation of the surface imido complex (≡SiO)2Ta(=N tBu)(CH2CMe2Ph) as a major species, which was characterized with EXAFS, 13C CP/MAS NMR, diffuse reflectance FTIR, elemental analyses, and chemical reactivity. The obtained material acts as an efficient heterogeneous catalyst for various oxo/imido heterometathesis transformations: imidation of ketones and DMF with N-sulfinylamines and condensation of N-sulfinylamines into sulfurdiimines and phenyl isocyanate into diphenylcarbodiimide.
Synthesis of polysubstituted 3H-pyrimidin-4-ones from cyanoacetamides under Vilsmeier conditions
Zhang, Zhiguo,Xue, Can,Liu, Xiao,Zhang, Qian,Liu, Qun
, p. 7081 - 7084 (2011/10/08)
A facile and efficient approach to a variety of 6-chloro-3,5-disubstituted 3H-pyrimidin-4-ones 2/6 from the readily available cyanoacetamides 1/5 under Vilsmeier conditions was developed, in which the Vilsmeier reagent plays multiple roles and the possible mechanism is discussed.
Iron-catalyzed epoxidation of aromatic olefins and 1,3-dienes
Schroeder, Kristin,Enthaler, Stephan,Join, Benoit,Junge, Kathrin,Beller, Matthias
experimental part, p. 1771 - 1778 (2010/09/11)
The combination of iron(III) chloride, pyridine-2,6-dicarboxylic acid and formamidine ligands allows for the epoxidation of styrenes and conjugated dienes in excellent chemoselectivity and yields.
Change of the favored routes of EI MS fragmentation when proceeding from N1, N1-dimethyl-N2-arylformamidines to 1,1,3,3-tetraalkyl-2-arylguanidines: Substituent effects
Raczynska, Ewa D.,Makowski, Mariusz,Gal, Jean-Francois,Maria, Pierre-Charles
body text, p. 762 - 771 (2011/09/12)
Although series of N1, N1-dimethyl-N 2-arylformamidines and of 1,1,3,3-tetraalkyl-2-arylguanidines are structurally analogous and similar electron-ionization mass spectral fragmentationmay be expected, they display important differences in the favored routes of fragmentation andconsequently in substituent effectsonion abundances. In the caseof formamidines, the cyclizationelimination process (initiated by nucleophilic attack of the N-amino atom on the 2-position of the phenyl ring) and formation of the cyclic benzimidazolium [M-H]+ ions dominates, whereas the loss of the NR2 group ismore favored for guanidines. In order to gain information on the most probable structures of the principal fragments, quantum-chemical calculations were performed on a selected set. A good linear relation between log{I[M-H]+I [M]+?} and σR+ constants of substituent at para position in the phenyl ring occurs solely for formamidines (r = 0.989). In the case of guanidines, this relation is not significant (r = 0.659). A good linear relation is found between log{I[M-NMe2]+/I [M]+?} and σp+ constants (r = 0.993). Copyright
Benzamidines, alkamidines and formamidines formed by use of aryl- and alkyliminodimagnesium: Molar ratio and structure of reagent governing the reaction
Okubo, Masao,Omote, Yasumasa
, p. 212 - 220 (2007/10/03)
In order to extend the the method for preparation of amidines using N-Mg reagents, aryl- and alkyliminodimagnesium [IDMg, ArN(MgBr)2 and RN(MgBr)2] were reacted with esters, amides, ortho- esters, acetals, aminoacetal and arene- and
Reactions of Aryliminodimagnesium with Some N,N-Dimethylcarboxamides and Benzonitriles Affording Various Types of Amidines. Correction of Previous Results on Formamidine Formation from N,N-Dimethylformamide
Okubo, Masao,Tanaka, Mikio,Murata, Yuri,Tsurusaki, Nobuyuki,Omote, Yasumasa,et al.
, p. 1965 - 1968 (2007/10/02)
Some symmetrical and unsymmetrical form- and benzamidines were prepared by the reaction of ArN(MgBr)2 with Ar'CN, HCONMe2 and related compounds in tetrahydrofuran.
Amidines. Part 31. pKa Values of N1,N1-Dialkyl-N2-phenylformamidines in Water-Ethanol Solutions
Oszczapowicz, Janusz,Jaroszewska-Manaj, Jolanta
, p. 1677 - 1680 (2007/10/02)
The pKa values of three series (30 compounds in all) of N1,N1-dialkyl-N2-phenylformamidines (XC6H4N=CHNRR) have been measured in water-ethanol mixtures.The obtained pKa values of the amidines have been correlated with Hammett-type substituent constants and the pKa values of the corresponding primary amines determined in the same solvent.The applicability of various ? values is discussed and it is shown that, in each case, for substituents on the phenyl ring at the amino nitrogen atom ?0 values should be used.It is found that the slopes of regression lines for correlations with Hammett-type constants depend on the substituents at the amino nitrogen atom, as well as on the solvent.
Formation of Amidines from Aryliminodimagnesium and N,N-Dimethylformamide. Novel Catalytic Mediation by Single Electron Transfer with Use of Nitrobenzenes
Okubo, Masao,Tanaka, Mikio,Matsuo, Koji
, p. 1005 - 1008 (2007/10/02)
N,N'-Diarylformamidines were obtained in good yields by the reaction of aryliminodimagnesium (ArN(MgBr)2) with N,N-dimethylformamide in the presence of nitrobenzene.Novel catalytic mediation by single electron transfer was disclosed.
