Latent Brønsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2041-2057 ◽  
Author(s):  
Rikuto Otsuka ◽  
Kazuo Maruhashi ◽  
Tomohiko Ohwada
Keyword(s):  
Aromatic Amines ◽  
Benzoyl Chloride ◽  
Aliphatic Amines ◽  
Acid Chlorides ◽  
Amide Formation ◽  
Brønsted Base ◽  
High Yields

Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N,N-dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Brønsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis

2019 ◽  
Author(s):  
Andrew Romine ◽  
Kin Yang ◽  
Malkanthi Karunananda ◽  
Jason Chen ◽  
Keary Engle
Keyword(s):  
Mechanistic Studies ◽  
Salvianolic Acid ◽  
Wide Range ◽  
Computational Data ◽  
Synthetic Utility ◽  
Directing Group ◽  
High Yields ◽  
Julia Olefination ◽  
Reaction Progress Kinetic Analysis

A weakly coordinating monodentate heteroaryl thioether directing group has been developed for use in Pd(II) catalysis to orchestrate key elementary steps in the catalytic cycle that require conformational flexibility in a manner that is difficult to accomplish with traditional strongly coordinating directing groups. This benzothiazole thioether, (BT)S, directing group can be used to promote oxidative Heck reactivity of internal alkenes providing a wide range of products in moderate to high yields. To demonstrate the broad applicability of this directing group, arene C–H olefination was also successfully developed. Reaction progress kinetic analysis provides insights into the role of the directing group in each reaction, which is supplemented with computational data for the oxidative Heck reaction. Furthermore, this (BT)S directing group can be transformed into a number of synthetically useful functional groups, including a sulfone for Julia olefination, allowing it to serve as a “masked olefin” directing group in synthetic planning. In order to demonstrate this synthetic utility, natural products (+)-salvianolic acid A and salvianolic acid F are formally synthesized using the (BT)S directed C–H olefination as the key step.

Phytocenotic selection of perennial grasses as a factor of increasing the productivity of mixed agrophytocenoses

2020 ◽  
Author(s):  
V.N. Zolotarev ◽  
◽  
I.S. Ivanov ◽  
O.N. Lyubtseva
Keyword(s):  
Perennial Grasses ◽  
New Varieties ◽  
The Creation ◽  
High Yields ◽  
Selection Of

Based on the analysis of data available in the literature and our own experimental material on phytocenotic selection of the stony stalk (Bromopsis inermis Holub.) the important role of competition between plants in the field for the creation of new varieties of perennial grasses that provide high yields of feed polyvid agrophytocenoses is shown.

Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively

Tetrahedron ◽  
2007 ◽  
Vol 63 (48) ◽  
pp. 12071-12080 ◽  
Author(s):  
Hidefumi Nakatsuji ◽  
Mami Morimoto ◽  
Tomonori Misaki ◽  
Yoo Tanabe
Keyword(s):  
Acid Chlorides ◽  
Robust Methods ◽  
Amide Formation

Addition of Aliphatic and Aromatic Amines to Catechol in Aqueous Solution Under Oxidizing Conditions

1989 ◽  
Vol 42 (3) ◽  
pp. 365 ◽  
Author(s):  
MK Manthey ◽  
SG Pyne ◽  
RJW Truscott
Keyword(s):  
Aqueous Solution ◽  
Aqueous Solutions ◽  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Substitution Pattern ◽  
Vinylogous Amides ◽  
The Stability

The oxidation of catechol in the presence of two aliphatic and aromatic amines has been investigated. In aqueous solutions of pH 7.0 and 11.7, the substitution pattern of the adduct was dependent on the type of amine used. Aromatic amines produced 4,5-disubstituted o-quinones, whereas aliphatic amines gave either 2,4,5-trisubstituted or 2,4-disubstituted o-quinone adducts. A rationale based upon the stability of vinylogous amides is presented to account for the observed substitution pattern.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

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