- A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes
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In comparison to the extensively studied metal-catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench-stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.
- Kaiser, Daniel,Tona, Veronica,Gon?alves, Carlos R.,Shaaban, Saad,Oppedisano, Alberto,Maulide, Nuno
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supporting information
p. 14639 - 14643
(2019/09/17)
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- Solvent-free synthesis of 2,2'-methylene-bis[4-tert-octyl-6-(2H-benzotriazolyl-2)]phenol
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The invention discloses a method for synthesizing 2,2'-methylene-bis[4-tert-octyl-6-(2H-benzotriazolyl-2)]phenol (UV-360) through solvent-free condensation. The method comprises the procedures of firstly, carrying out condensation dehydration on di-n-propyl amine and formaldehyde or paraformaldehyde, which serve as raw materials, at the temperature of about 120 DEG C so as to synthesize di(n-propylamino)methane, and then, carrying out condensation with 2-(2'-hydroxyl-5'-tert-octylphenyl)benzotriazole at the temperature of about 160 DEG C under the catalysis of sodium hydroxide under solvent-free conditions, thereby synthesizing the UV-360. According to the method, no high-boiling solvent is used, so that problems of the existing methods are solved; and di-n-propyl amine is easy to recover and recycle, and the product quality is high.
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0049; 0051
(2017/08/29)
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- Synthesis, characterization, and anti-amoebic screening of core-modified 5,20-bis{2-{[(alkyl)(alkyl′)amino]methyl}ferrocen-1-yl}-10,15-diphenyl-21, 23-dithiaporphyrin (=1,1″-(10,15-diphenyl-21,23-dithiaporphine-5,20-diyl) bis[2-{[(alkyl)(alkyl′)amino]methyl}ferrocene]) derivatives
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The synthesis of the first bis-ferrocenyl-substituted core-modified porphyrins, 5,20-bis{2-{[(alkyl)-(alkyl′)amino]methyl}ferrocen-1-yl}-10, 15-diphenyl-21,23-dithiaporphyrin derivatives 6a - 6j, via a multistep route is reported (Schemes 1, 2, and 4). The synthesis was carried out through acid-catalyzed (BF3 ? Et2O) condensation of 1,1″- [thiophene-2,5-diylbis(hydroxymethyl)]bis[2-{[(alkyl)(alkyl′)amino]methyl} ferrocenes] 4a - 4j with 2,2′-[thiophene-2,5-diylbis(phenylmethylene)] bis[1H-pyrrole] (5b) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (=4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; DDQ). Characterization of the compounds was done at each step by means of various spectroscopic techniques. The final compounds were screened for in vitro anti-amoebic activity against the strain HM1:IMSS of E. histolytica (Table 2).
- Bhat, Abdul R.,Bhat, Asif I.,Athar, Fareeda,Azam, Amir
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experimental part
p. 1644 - 1656
(2009/10/16)
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- Process for preparing substituted 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl-phenols]
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A method is described for preparing compounds of Formula I and Formula II: STR1 R1 is an alkyl group of one to twelve carbon atoms or a cycloalkyl group of five to eight carbons, X is chloro or hydrogen, and R2 is an alkoxy group having one to twelve carbons. In accordance with the method: (a) a bis(dialkylamino)methane is formed, preferably by reacting a dialkylamine of the formula HNR3 R4 (wherein R3 and R4 are independently alkyl groups having three or more carbons) and a solid formaldehyde material to produce the corresponding bis(dialkylamino)methane, (b) a monomer of Formula III or IV STR2 in which R1 is an alkyl group of one to twelve carbons or a cycloalkyl group of five to eight carbons, X is chloro or hydrogen and R2 is an alkoxy group having one to twelve carbon atoms, is mixed with an alkaline catalyst with heating at a temperature high enough to drive off the liquid formed in the reaction, (c) the product of steps (a) and (b) are combined and stirred at a temperature sufficient to drive the reaction for six to fourteen hours, and (d) thereafter the resulting compound of Formula I is collected.
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- A Novel Synthesis of Diaminomethanes
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Diaminomethanes have been synthesized by reaction of 1,3-benzodioxole and 1,3-benzoxathiole with a double amount of sodium dialkyl and alkyl aryl amides.
- Melis, Stefana,Monni, Francesca,Piras, Pier Paolo,Sotgiu, Francesca
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