36635-56-0Relevant academic research and scientific papers
Br?nsted Acid Organocatalyzed Three-Component Hydroamidation Reactions of Vinyl Ethers
Smajlagic, Ivor,Carlson, Brenden,Dudding, Travis
, p. 4171 - 4181 (2021)
Hydroamidation of carbon-carbon double bonds is an attractive strategy for installing nitrogen functionality into molecular scaffolds and, with it, increasing molecular complexity. To date, metal-based approaches have dominated this area of chemical synth
Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
, p. 14213 - 14222 (2021/09/07)
A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
Phenyl pyrrole compound and application thereof in bactericidal activity
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Paragraph 0137; 0139, (2020/08/17)
The invention provides a novel phenyl pyrrole compound, and the phenyl pyrrole compound shows good bactericidal activity and can be used for preparing a broad-spectrum plant bactericide. In addition,the synthesis route is simple, the operation is convenient, the synthesis cost is reduced, and ecological environment pollution to soil, surface water, underground water and the like is avoided.
SUBSTITUTED IMIDAZO[1,5-A]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
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Paragraph 00241, (2016/06/01)
The invention provides substituted imidazo[1,5-a]pyrimidines and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,5-a]pyrimidine compounds described herein include substituted 2,4-dimethyl-N-phenylimidazo[1,5-a]pyrimidine-8-carboxamide compounds and variants thereof.
A 2-fluoro-4-methyl sulfonyl methyl isonitriles method for the synthesis of
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Paragraph 0021; 0022, (2017/03/08)
The invention discloses a synthesis method of 2-fluoro-4-toluenesulfonylmethyl isocyanide. The method comprises the following steps: with sodium p-tolylsulfinate as a raw material, carrying out similar Mannich condensation and amide dehydration reaction to prepare tolylsulfonylmethyl isocyanide; adding a hydrofluoric acid aqueous solution and an Ni-CO catalyst to tolylsulfonylmethyl isocyanide; and fully reacting under nitrogen protection, and carrying out suction filtration, washing and drying to obtain faint yellow crystal 2-fluoro-4-toluenesulfonylmethyl isocyanide, wherein the yield reaches over 92%, and the purity is 99.8%. The synthesis method has the advantages of being available in reaction raw materials, mild in condition, high in yield, suitable for industrial production and the like.
4 - (2,2-difluoro -1,3-Benzodioxole-4-yl) pyrrole-3-nitrile synthetic method
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Paragraph 0046; 0060; 0069; 0076, (2018/07/10)
The invention discloses a synthetic method of 4-(2,2-difluoro-1,3-benzodioxole-4-yl)pyrrole-3-nitrile. The method comprises the following steps of: preparing an intermediate 2,2-difluorobenz-1,3-dioxole through reacting catechol with dibromodifluoromethane, and preparing an intermediate 2-cyano-3-(2,2-difluorobenz-1,3-dioxole-4-yl)-2-acrylate. The fludioxonil prepared by the synthetic method provided by the invention has the purity of more than 99.0% and the total yield of more than 45.0%; the synthetic method has the advantages of cheap and easily available raw materials, simple process, high product yield in each step, good purity, low production cost, applicability to batch industrial production and the like.
Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
Chen, Jiajia,Guo, Wei,Wang, Zhenrong,Hu, Lin,Chen, Fan,Xia, Yuanzhi
, p. 5504 - 5512 (2016/07/13)
The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.
Alkyl sulfinates: Formal nucleophiles for synthesizing TosMIC analogs
Lujan-Montelongo, J. Armando,Estevez, Angel Ojeda,Fleming, Fraser F.
, p. 1602 - 1605 (2015/03/04)
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
Catalytic, enantioselective α-additions of isocyanides: Lewis base catalyzed Passerini-type reactions
Denmark, Scott E.,Fan, Yu
, p. 9667 - 9676 (2007/10/03)
The generality of catalytic, enantioselective α-additions of isocyanides to aldehydes has been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide (R,R)-1b provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, heteroaromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides whereas a low-temperature methanol quench followed by basic workup afforded the α-hydroxy methyl esters. The reaction is also successful for other isocyanides, albeit with reduced enantioselectivity. Reaction conditions, particularly the rate of addition of the isocyanide was found to be crucial for good yields and high selectivities.
Synthesis of a 10-oxo-bilirubin: Effects of the oxo group on conformation, transhepatic transport, and glucuronidation
Chen, Qingqi,Huggins, Michael T.,Lightner, David A.,Norona, Wilma,McDonagh, Antony F.
, p. 9253 - 9264 (2007/10/03)
Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C(10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C(10). The change from CH2 to C=O, from sp3 to sp2, is designed to stress the molecule at its hinge and relax its conformation. Such compounds have been suggested as potential oxidative metabolites of bilirubin in vivo. 10-Oxo-mesobilirubin-XIIIα (1) is a red crystalline solid, unlike its parent, mesobilirubin-XIIIα, which is a bright yellow solid. It is surprisingly polar, relative to the parent, yet it does not exhibit a significantly larger bicarbonate/chloroform partition coefficient. Like the parent, 1 appears to adopt an intramolecularly hydrogen-bonded ridge-tile-like conformation. In normal rats, 1 is metabolized to acylglucuronides, which are secreted into bile, but a portion of the administered dose is secreted into bile intact. In mutant rats (Gunn rats) lacking bilirubin glucuronyl transferase, 1 was excreted efficiently in bile in unchanged form, unlike the parent with a methylene group at C(10). Thus, introduction of the oxygen function at C(10) has little effect on hepatic uptake but a dramatic effect on canalicular secretion into bile.
