Tandem Synthesis of Amides and Secondary Amines from Esters with Primary Amines under Solvent-Free Conditions

2014 ◽  
Vol 356 (11-12) ◽  
pp. 2653-2660 ◽  
Author(s):  
Jeongbin Lee ◽  
Senthilkumar Muthaiah ◽  
Soon Hyeok Hong
2016 ◽  
Vol 71 (2) ◽  
pp. 95-104 ◽  
Author(s):  
Sara Ebrahimi ◽  
Safoura Saiadi ◽  
Simin Dakhilpour ◽  
Seyed Nezamoddin Mirsattari ◽  
Ahmad Reza Massah

AbstractA variety ofN-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a–e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.


Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1761 ◽  
Author(s):  
Adam P. Zarecki ◽  
Jacek L. Kolanowski ◽  
Wojciech T. Markiewicz

Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.


2021 ◽  
Author(s):  
Narender Nama ◽  
Vasu Amrutham ◽  
Naresh Mameda ◽  
Krishna Sai Gajula ◽  
Divya rohini yennamaneni ◽  
...  

This study reports a straightforward heterogonous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and...


2018 ◽  
Vol 73 (1) ◽  
pp. 43-74 ◽  
Author(s):  
Cindy Döring ◽  
Peter G. Jones

AbstractThe reaction of (tht)AuX (X=Cl or Br; tht=tetrahydrothiophene) with various primary amines L leads to products of the form [L2Au]+X−. Packing diagrams of the corresponding structures are dominated by N–H···X hydrogen bonds and (in some cases) aurophilic contacts. The cyclohexylamine derivative was already known as its dichloromethane ⅔-solvate; we have isolated the solvent-free compound and its pentane ¼-solvate, which all show different packing patterns. With acyclic secondary amines, the products are more varied; LAuX and [L2Au]+[AuX2]− were also found. These gold(I) products were generally formed in satisfactory quantities. The attempted oxidation to Au(III) derivatives with PhICl2 or Br2 proved impossible for the primary amine derivatives [although isopropylamine-trichloridogold(III) was obtained unexpectedly from the corresponding cyanide] and unsatisfactory for the secondary amine derivatives. Products LAuX3 and [L2AuX2]+[AuX4]− were identified but were formed in disappointing yields. In isolated cases protonated products (LH)+[AuCl4]−, (LH+)3[AuCl4]−(Cl−)2 or [(Et2N)2CH]+[AuBr4]− were formed, presumably by involvement of the dichloromethane solvent and/or adventitious water. Here also the yields were poor, and some products arose as mixtures. Direct reaction of amines with AuCl3 or (tht)AuX3 was also unsuccessful. All products were characterized by X-ray structure analysis.


2013 ◽  
Vol 9 ◽  
pp. 2344-2353 ◽  
Author(s):  
Sudipta Pathak ◽  
Kamalesh Debnath ◽  
Animesh Pramanik

A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.


2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Davood Habibi ◽  
Payam Rahmani ◽  
Ziba Akbaripanah

N-formylation of primary and secondary amines was carried out with formic acid in the presence of silica sulfuric acid under solvent-free conditions to give the corresponding formamides in excellent yield and short reaction times.


2019 ◽  
Vol 48 (10) ◽  
pp. 3447-3452 ◽  
Author(s):  
Alexandra A. Ageshina ◽  
Grigorii K. Sterligov ◽  
Sergey A. Rzhevskiy ◽  
Maxim A. Topchiy ◽  
Gleb A. Chesnokov ◽  
...  

A single catalyst for solvent-free Buchwald–Hartwig amination with both primary and secondary amines.


2011 ◽  
Vol 49 (2) ◽  
pp. 375-380 ◽  
Author(s):  
Quan-Sheng Ding ◽  
Ji-Lei Zhang ◽  
Jiu-Xi Chen ◽  
Miao-Chang Liu ◽  
Jin-Chang Ding ◽  
...  

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