38951-44-9Relevant academic research and scientific papers
Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines
Yin, Jiawen,Zhang, Jingyu,Cai, Changqun,Deng, Guo-Jun,Gong, Hang
, p. 387 - 392 (2019)
A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.
A non-catalyst non-promoter under the conditions of amide derivatives of aromatic amine with transfers the amine reaction
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Paragraph 0047; 0048, (2019/03/28)
The present invention discloses a non-catalyst under the condition of non-accelerator [...] amide derivatives of aromatic amine with transfers the amine reaction, yield of synthetic N - aryl amide derivatives. The method has a wide range of the substrate, its raw materials and cheap and easy to obtain acylation reagent, the reaction yield is high, one-step reaction, low cost, high reaction selectivity, simple operation and the like. Adopting this method can be gram scale can realize the high yield of the synthesis of drug molecules. Therefore, the method in the N - aryl amide derivatives of synthesis application field has very good application prospect. The method overcomes the existing technologies such as the reaction reagent toxicity is large, the need to use different type catalyst, synthesis method and the cost is high, more reaction steps, more byproducts and the like.
Method of N-formylating amines with a phosphonic anhydride
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Page/Page column 21; 22; 23; 24; 29, (2018/02/28)
A method for N-formylating an amine that includes reacting the amine and a formamide compound in the presence of a phosphonic anhydride to form an N-formylated amine. The phosphonic anhydride is present in an amount of 5-100 mol % relative to a total number of moles of the amine, and the reacting is performed for 1-24 hours at a temperature of 45-100° C.
Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
Hu, Zhongyan,Dong, Jinhuan,Men, Yang,Lin, Zhichen,Cai, Jinxiong,Xu, Xianxiu
supporting information, p. 1805 - 1809 (2017/02/05)
A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.
Rhodium-catalyzed ortho C-H bond activation of arylamines for the synthesis of quinoline carboxylates
Gadakh, Sunita K.,Dey, Soumen,Sudalai
, p. 2969 - 2977 (2016/03/12)
The rhodium catalyzed annulation of anilines with alkynic esters allowing for the high-yield synthesis of quinoline carboxylates with excellent regioselectivity is described. This unprecedented reaction employs either formic acid as the C1 source and reductant or copper(ii) as the oxidant and is proposed to proceed via rhodacycle of in situ generated amide and enamine ester followed by ortho C-H activation of arylamines with rhodium as the catalyst.
Iron-Catalyzed C-N Bond Formation via the Beckmann Rearrangement
Jefferies, Latisha R.,Weber, Savannah R.,Cook, Silas P.
supporting information, p. 331 - 334 (2015/02/19)
A simple, iron-based catalytic system allows for facile Beckmann rearrangement of various oximes. The mild conditions avoid the use of harsh or expensive acids, and the reactions do not require an inert atmosphere. Additionally, a range of amides can be accessed through this transformation.
Combretastatin A-4 inspired novel 2-aryl-3-arylamino-imidazo-pyridines/ pyrazines as tubulin polymerization inhibitors, antimitotic and anticancer agents
Sanghai, Nitesh,Jain, Vaibhav,Preet, Ranjan,Kandekar, Somnath,Das, Sarita,Trivedi, Neha,Mohapatra, Purusottam,Priyadarshani, Garima,Kashyap, Maneesh,Das, Dipon,Satapathy, Shakti Ranjan,Siddharth, Sumit,Guchhait, Sankar K.,Kundu, Chanakya N.,Bharatam, Prasad V.
supporting information, p. 766 - 782 (2014/06/10)
Based on the pharmacophoric features of the natural product combretastatin A-4 (CA-4) and its synthetic analogues that inhibit tubulin polymerization, a series of novel 2-aryl-3-arylamino-imidazo-pyridines/pyrazines as potential antitubulin anticancer agents were designed. They were synthesized by a one-pot method involving preparation of isocyanides from the anilines via formylation and subsequent dehydration followed by their reactions with heterocyclic-2- amidines and aldehydes. Compounds 1, 2, 14, and 15 were found to exhibit significant tubulin polymerization inhibition and disruption of tubulin-microtubule dynamics similar to that of CA-4. They showed potent anticancer activities in kidney, breast and cervical cancer cell lines, and relatively low toxicity to normal cells, compared to CA-4. The compounds induced DNA and chromosomal damage, and apoptosis via cell cycle arrest in the G2/M phase. The molecular docking and molecular dynamics (MD) simulation studies revealed that disruption of microtubule dynamics might occur by interaction of the compounds at the colchicine binding site of the α,β-tubulin heterodimer interface, similar to that of CA-4. Molecular modelling analysis showed that two of the three methoxy groups at ring A of all four potent compounds (1, 2, 14, and 15) were involved in bifurcated hydrogen bonding with Cysβ241, an important molecular recognition interaction to show tubulin inhibitory activity. In comparison to CA-4, the bridging NH and the imidazo-pyridine/pyrazine moieties in the title compounds provide flexibility for attaining the required dihedral relationship of two aryls and additional pharmacophoric features required for the interaction with the key residues of the colchicine binding site.
A novel method for preparing isocyanides from N-substituted formamides with chlorophosphate compounds
Kobayashi, Genki,Saito, Tateo,Kitano, Yoshikazu
experimental part, p. 3225 - 3234 (2011/11/30)
Treatment of N-substituted formamides with chlorophosphate compounds such as PhOPOCl2, EtOPOCl2, Me2NPOCl2, and (PhO)2POCl and tertiary amines such as triethylamine, pyridine, and N,N-diisopropylethylamine produced the corresponding isocyanides in high yields. This method can be used to prepare various alkyl and aryl isocyanides. Georg Thieme Verlag Stuttgart · New York.
2,4-diaminopyridopyrimidine Inhibitors of Dihydrofolate Reductase from Pneumocystis carinii and Toxoplasma gondii
Rosowsky, Andre,Forsch, Ronald A.,Queener, Sherry F.
, p. 2615 - 2620 (2007/10/03)
Six previously unknown 2,4-diamino-6-(anilinomethyl)- and 2,4-diamino-6-pyridopyrimidines (5-10) were synthesized from 2,4-diamino-6-(bromomethyl)pyridopyrimidine hydrobromide (11*HBr) by treatment with the appropriate aniline or N-methylaniline in dimethylformamide at room temperature, with or without NaHCO3 present.Compounds 5-10 were tested as inhibitors of dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, and rat liver as a part of a larger effort directed toward the discovery of lipophilic nonclassical antifolates combining high enzyme selectivity and high potency.Of the six analogues tested, the most potent and selective against T. gondii DHFR was 2,4-diamino-6-pyridopyrimidine (7), which had an IC50 of 0.0047 μM against this enzyme as compared with 0.026 μM against the rat liver enzyme.The potency of 7 against T. gondii DHFR was similar to that of trimetrexate (TMQ, 1) and piritrexim (PTX, 2) but was >500-fold greater than that of trimethoprim (TMP, 3).However, while 7 was more selective than either TMQ (19*) or PTX (63*) against this enzyme, its selectivity in comparison with TMP was 8-fold lower. 2,4-Diamino-6-pyridopyrimidine (6) was 17-fold less active than 7 and was also less selective. 2,4-Diamino-6-pyridopyrimidine (10) had an IC50 of 0.022 μM against P. carinii DHFR and was comparable in potency to TMQ and PTX.The species selectivity of 10 for P. carinii versus rat liver DHFR was greater than that of either TMQ (21-fold) or PTX (31-fold).On the other hand, even though 10 was slightly more active than TMQ against the P. carinii enzyme, its selectivity was 7-fold lower than that of TMP.Thus, the goal of combining high enzyme binding activity, which is characteristic of the fused-ring compounds TMQ and PTX, with high selectivity for T. gondii and P. carinii DHFR versus rat liver DHFR, which is characteristic of the monocyclic compound TMP, remained unmet in this limited series.
The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 21. A Mild Process For The Preparation of 10-Alkyl-9-acridanones And It's Application To The Synthesis of Acridone Alkaloids
Coppola, Gary M.,Schuster, Herbert F.
, p. 957 - 964 (2007/10/02)
10-Substituted-9-acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2-cyclohexen-1-one.The initially formed product, the 1,2-dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone.This methodology is applicable to the synthesis of acridone natural products.Two alkaloids, 1,2,3-trimethoxy-10-methylacridone (9) and evoxanthine (10), were prepared from 4,5,6-trimethoxy-N-methylisatoic anhydride and 6-methoxy-4,5-methylenedioxy-N-methylisatoic anhydride respectively.In these trioxygenated systems, palladium-on-charcoal must be used to aromatize the penultimate intermediate.
