493-77-6Relevant articles and documents
Diverse reactivity of rhodium β-(tetraphenyl)tetraphenyl porphyrin chlorides with benzonitrile: Formation of Rh porphyrin arene and imine complexes
Zhou, Xiang,Tse, Man Kin,Wu, De-Dong,Mak, Thomas C.W.,Chan, Kin Shing
, p. 80 - 86 (2000)
The reaction of rhodium trichloride with β-(tetraphenyl)tetraphenyl porphyrin, H2(tpp)(Ph)4, and β-(tetraphenyl)tetrakismesityl porphyrin, H2(tmp)(Ph)4, in refluxing benzonitrile gave novel rhodium porphyrin chl
Direct Synthesis of a Covalent Triazine-Based Framework from Aromatic Amides
Yu, Soo-Young,Mahmood, Javeed,Noh, Hyuk-Jun,Seo, Jeong-Min,Jung, Sun-Min,Shin, Sun-Hee,Im, Yoon-Kwang,Jeon, In-Yup,Baek, Jong-Beom
, p. 8438 - 8442 (2018)
There have been extensive efforts to synthesize crystalline covalent triazine-based frameworks (CTFs) for practical applications and to realize their potential. The phosphorus pentoxide (P2O5)-catalyzed direct condensation of aromatic amide instead of aromatic nitrile to form triazine rings. P2O5-catalyzed condensation was applied on terephthalamide to construct a covalent triazine-based framework (pCTF-1). This approach yielded highly crystalline pCTF-1 with high specific surface area (2034.1 m2 g?1). At low pressure, the pCTF-1 showed high CO2 (21.9 wt % at 273 K) and H2 (1.75 wt % at 77 K) uptake capacities. The direct formation of a triazine-based COF was also confirmed by model reactions, with the P2O5-catalyzed condensation reaction of both benzamide and benzonitrile to form 1,3,5-triphenyl-2,4,6-triazine in high yield.
Butyllithium-induced Cyclotrimerisation Reactions of Organic Nitriles: Solvent Dependency, Crystal and Solution Structures of Lithio Triazine Intermediates and an Unexpected Rearrangement of Dihydrotriazino Anions
Armstrong, David R.,Clegg, William,MacGregor, Murray,Mulvey, Robert E.,O'Neil, Paul A.
, p. 608 - 610 (1993)
Sequential addition of ButCN and PhCN (2 equiv.) to BunLi in the presence of tetrahydrofuran (THF) produces an isolable lithio 1,4-dihydrotriazine tris(THF) solvate, characterised by both NMR spectroscopic and X-ray crystallographic methods, which converts to a 1,2-dihydro arrangement on methanolysis.
Direct synthesis of covalent triazine-based frameworks (CTFs) through aromatic nucleophilic substitution reactions
Chen, Tao,Li, Wen-Qian,Hu, Wei-Bo,Hu, Wen-Jing,Liu, Yahu A.,Yang, Hui,Wen, Ke
, p. 18008 - 18012 (2019)
Despite extensive efforts, only three main strategies have been developed to synthesize covalent triazine-based frameworks (CTFs) thus far. We report herein a totally new synthetic strategy which allows C-C bonds in the CTFs to be formed through aromatic nucleophilic substitution reactions. The as-synthesized CTF-1 and CTF-2 exhibited photocatalytic water splitting activity comparable to the CTFs made using ionothermal or Br?nsted acid-catalyzed polymerization. Interestingly, CTF-2 distinguished itself by its two-photon fluorescence (emission at ～530 nm under irradiation at either 400 nm or 800 nm).
Functionalized fluorenes via dicationic electrophiles
Stentzel, Michael R.,Klumpp, Douglas A.
, p. 1675 - 1677 (2019)
Dicationic fluorenyl cations are shown to react with nitriles to provide amide-functionalized fluorenes. A similar reaction with alcohols gives ether derivatives. The chemistry is initiated by the reactions of N-heterocyclic ketones in a superacidic solution. This leads to cyclizations involving 2-biphenyl groups and formation of the reactive fluorenyl cations.
Synthetic and theoretical MO calculational studies of lithiotriazine intermediates produced during alkyllithium-induced cyclotrimerisation reactions of organic nitriles, and comparison of their structures with that of a methylmagnesiotriazine derivative
Armstrong, David R.,Henderson, Kenneth W.,MacGregor, Murray,Mulvey, Robert E.,Ross, Michael J.,et al.
, p. 79 - 94 (1995)
Benzonitrile can be readily cyclotrimerised by treatment with a suitable alkyllithium to give a simple triazine or to a solvated lithiodihydrotriazine derivative.Which cyclic product dominates depends mainly on the source of the active Li+ cation (n-butyllithium, t-butyllithium and tetramethylguanidinolithium are considered here), and on the solvent employed.X-ray crystallographic studies on a representative compound show that the lithio species exists as a mononuclear, contact ion pair structure, with the triazine ring in a 1,4-dihydro state.On reaction with theGrignard reagent, MeMgCl, this compound gives a methylmagnesiodihydrotriazine, which has also been crystallographically characterised and found to closely resemble its lithio precursor.Ab initio MO calculations on model systems reveal that the 1,4-dihydrotriazine arrangements is energetically preferred to the 1,2-dihydro alternative irrespective of the counterion (Li+ or H+) present.A theoretical investigation of the methanolysis of the lithio species indicates that the formation of an intermediate MeOH complex, with the alcohol attached to a ring N atom and not to Li+, directs the reaction towards ultimate formation of a 1,2-dihydrotriazine.Keywords: Triazine; Lithium; Magnesium; Ab initio; Crystal structure
One-pot synthesis of new heterocycles: 2,4-disubstituted 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidines
Herrera, Antonio,Martínez-Alvarez, Roberto,Chioua, Rachid,Chioua, Mourad
, p. 2149 - 2151 (2003)
The reaction of 1-benzosuberone with nitriles in the presence of triflic anhydride affords in good yields 2,4-diaryl substituted 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidines, a new class of heterocycle.
Solvothermal Reactions in and with Nitriles
Thiele, Günther,Wagner, Bettina,Dehnen, Stefanie
, p. 5329 - 5334 (2015)
Solvothermal reactions and in situ reductions in nitriles yield a variety of new metal complexes and organometallic compounds including ligands of dimers, trimers, and tetramers of the organic solvent upon (oxidative) C-C and/or C-N bond formation and destruction.
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Swamer et al.
, p. 43,44,45 (1951)
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Preparation method of multipurpose compound s-triazine derivative
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Paragraph 0043-0050, (2021/06/26)
The invention provides a preparation method of a s-triazine derivative, which is characterized in that an aryl nitrile compound is used as a substrate, lithium bis (trifluoromethanesulfonimide) is used as a catalyst, and the s-triazine derivative is obtained through a cyclopolymerization reaction. Compared with the prior art, the method has the advantages that a catalytic system is simple and easy to obtain, too high or too low rigorous reaction temperature is not needed, the reaction condition is mild, the reaction time is short, the post-treatment is simple, and the obtained s-triazine derivative has very high yield and is suitable for large-scale production.
Synthesis method of cyanoacrylate compound
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Paragraph 0020-0021; 0022-0023; 0024; 0025-0026, (2021/09/21)
The method comprises the following reaction steps: a compound (1) reacts with a compound (2) to directly prepare a compound (3), and is characterized in that the reaction is carried out in a molten state. Compound (1). Compound (2). Compound (3).
Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets
Hua, Manli,Song, Jinliang,Huang, Xin,Liu, Huizhen,Fan, Honglei,Wang, Weitao,He, Zhenhong,Liu, Zhaotie,Han, Buxing
supporting information, p. 21479 - 21485 (2021/08/23)
Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.
