25105-59-3Relevant academic research and scientific papers
Direct aziridination of nitroalkenes affording N-alkyl-C-nitroaziridines and the subsequent Lewis acid mediated isomerization to β-nitroenamines
Hao, Feiyue,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 5442 - 5445 (2017)
A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.
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.
Synthesis of new azepino[3,4,5-cd]indole derivatives
Hayes,Hayler,Walsgrove,Wicks
, p. 209 - 212 (2007/10/03)
New 2-oxoazepino[3,4,5-cd]indole derivatives were formed by the reaction of the tosylate SKandF 98339 with N-alkyl and N-arylidenepropylamines in moderate yield.
Separation of Ring Polar and Resonance Effects on the Rate Constants for Uncatalyzed N-Arylidenepropylamine Formation in Methanol
Toullec, Jean,Milin, Didier
, p. 2840 - 2847 (2007/10/02)
Rate constants are reported for the reaction of a series of 19 ring-substituted benzaldehydes with propylamine in methanol and in O-d-methanol at different temperatures and of three of them with 2-methoxyethylamine and 2,2-dimethoxyethylamine.The large di
