326591-73-5Relevant academic research and scientific papers
Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
Ramsden, Jeremy I.,Heath, Rachel S.,Derrington, Sasha R.,Montgomery, Sarah L.,Mangas-Sanchez, Juan,Mulholland, Keith R.,Turner, Nicholas J.
, p. 1201 - 1206 (2019/01/21)
The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.
A metallopeptoid as an efficient bioinspired cooperative catalyst for the aerobic oxidative synthesis of imines
Chandra Mohan, Darapanani,Sadhukha, Arghya,Maayan, Galia
, p. 139 - 144 (2017/10/16)
Enzymatic catalysis is largely based on intramolecular cooperativity between a metal center and functional organic molecules located on one scaffold. Inspired by this concept we have designed the metallopeptoid trimer BT, which is a unique intramolecular cooperative oxidation catalyst incorporating two catalytic centers, phenanthroline-copper and TEMPO, as well as one non-catalytic benzyl group. Herein we explore the capability of BT to act as an efficient catalyst for the oxidative synthesis of imines, which are versatile intermediates in the fine chemicals and pharmaceutical industries. We demonstrate that BT, combined with CuI, can catalyze the production of benzyl, aryl, heteroaryl, allylic and aliphatic imines from various alcohols and amines with a turn-over-number up to 45 times higher than this achieved when phenanthroline, copper and TEMPO are mixed in solution. Moreover, in low catalyst(s) loading, BT enables transformations that are not possible when a mixture of the individual catalysts is employed.
Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction
Gangadasu,Narender,Bharath Kumar,Ravinder,Ananda Rao,Ramesh,China Raju,Jayathirtha Rao
, p. 8398 - 8403 (2007/10/03)
Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed.
Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions
Byung, Tae Cho,Sang, Kyu Kang
, p. 5725 - 5734 (2007/10/03)
A simple and convenient procedure for reductive amination of aldehydes and ketones using sodium borohydride activated by boric acid, p-toluenesulfonic acid monohydrate or benzoic acid as reducing agent under solvent-free conditions is described.
Base induced carbon-nitrogen (C=N) double bond migration in Schiff bases
Gangadasu,Narender,China Raju,Jayathirtha Rao
, p. 2598 - 2600 (2007/10/03)
Various Schiff bases have been prepared to study base induced carbon-nitrogen double bond migrations. Schiff bases derived from aliphatic aldehydes display highest selectivity. Hydrolysis of the resulting rearranged Schiff base provides an entry to make amines from aldehydes. The reaction has possible practical application.
A new 'one-pot' synthesis of 2-substituted 3-nitro pyrrolidines through a multicomponent domino reaction
Baricordi, Nikla,Benetti, Simonetta,Biondini, Gisella,De Risi, Carmela,Pollini, Gian P.
, p. 1373 - 1375 (2007/10/03)
An efficient 'one-pot' synthesis of the title compounds based on a multicomponent domino reaction between imines and 3-nitro-1-propanol methanesulfonate has been developed.
Rapid and diverse route to natural product-like biaryl ether containing macrocycles
Cristau, Pierre,Vors, Jean-Pierre,Zhu, Jieping
, p. 7859 - 7870 (2007/10/03)
A two-step sequence involving an Ugi four-component reaction and an intramolecular nucleophilic aromatic substitution (SNAr) has been developed for the rapid access to biaryl-ether containing macrocycles. In the course of this study, we documented that ammonium chloride can promote the Ugi-4CR in non-polar aprotic solvent (toluene) without the interference of an alternative Passerini reaction. Solid phase synthesis of macrocycles by this two-step sequence was also developed using polymer (Wang resin) supported α-(4′-fluoro-3′-nitro)phenethyl isocyanoacetate as one of the inputs.
