121004-44-2Relevant articles and documents
Assessment of a reductive amination route to methyl(3-nitrobenzyl)amine hydrochloride
Connolly, Terrence J.,Constantinescu, Anton,Lane, Tim S.,Matchett, Michael,McGarry, Patrick,Paperna, Mariya
, p. 837 - 842 (2005)
During the development of a sodium borohydride mediated reductive animation of 3-nitrobenzaldehyde with methylamine, studies revealed that partial reduction of the nitro group occurred, and potentially dangerous azo- and azoxy-containing products were gen
Stable carbamate pathway towards organic-inorganic hybrid perovskites and aromatic imines
Hur, Nam Hwi,Kim, Sun Joo,Lee, Byeongno,Lee, Kyu Hyung,Lim, Byung Wook,Nam, Wonwoo,Park, Hee Sun,Park, Young Jun
, p. 38055 - 38062 (2020/11/02)
Methyl ammonium methyl carbamate (MAC), formulated as CH3NH3+CH3NHCO2-, was synthesized by reacting liquid methylamine with supercritical CO2, and its structure was refined by single-crystal X-ray diffraction. MAC is a white crystalline salt and is as reactive as methylamine, and is a very efficient alternative to toxic methylamine. We were able to produce hybrid perovskite MAPbI3 (MA = methyl ammonium) by grinding MAC with PbI2 and I2 at room temperature, followed by storing the mixed powder. Moreover, this one-pot method is easily scalable for the large-scale synthesis of MAPbI3 in a small vessel. We have also investigated the reactivity of MAC towards aromatic aldehydes in the absence of solvent. The solventless reactions afforded imines as exclusive products with over 97% yield, which show higher selectivity than the methylamine-based synthesis. Complete conversions were typically accomplished within 3 h at 25 °C. The results of this study emphasize the importance of solid carbamates such as MAC to develop an environmentally friendly process for the synthesis of various amine-based materials on the industrial scale.
Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction
Bakulina, Olga,Dar'In, Dmitry,Krasavin, Mikhail
, p. 3989 - 3998 (2018/06/08)
The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.
Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction
Blümel, Marcus,Chauhan, Pankaj,Hahn, Robert,Raabe, Gerhard,Enders, Dieter
supporting information, p. 6012 - 6015 (2015/01/08)
A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogeni
