5469-56-7

Usage

Synonyms

DPP

Class

Pyrrolidines (five-membered nitrogen-containing heterocycles)

Physical state

Solid

Color

White to off-white

Melting point

107-110°C

Solubility

Sparingly soluble in water, soluble in organic solvents

Applications

a. Precursor in the synthesis of pharmaceuticals
b. Development of drugs with potential psychoactive and analgesic properties
c. Synthesis of other organic compounds
d. Derivatives used in organic electronics

Biological activities

a. Potential antioxidant
b. Potential anti-inflammatory agent

InChI:InChI=1/C16H15NO/c18-16-12-11-15(13-7-3-1-4-8-13)17(16)14-9-5-2-6-10-14/h1-10,15H,11-12H2

Upstream product

• 33685-12-0 N-(1-phenylbut-3-yn-1-yl)aniline 
• 62-53-3 aniline 
• 2051-95-8 succinylbenzene 
• 17649-94-4 N-phenyl 3-benzoylpropionamide 
• 60773-91-3 β-benzalpropionic acid anilide 
• 103-84-4 Acetanilid 
• 96-09-3 styrene oxide 
• 119690-92-5 4-Hydroxy-4,N-diphenyl-butyramide 
• 101118-77-8 3-chloro-1,5-diphenyl-pyrrolidin-2-one 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 

Relevant academic research and scientific papers

One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow

Owing to their wide range of biological properties, γ-aminobutyric acid derivatives (GABA) have been extensively studied and found noteworthy industrial applications. However, atom-economical and efficient processes for their production are scarce and would greatly benefit from further investigations. Herein, we demonstrate that an iridium-based photocatalyst promotes the direct reductive cross-coupling of imines with olefins upon irradiation with visible light to give GABA derivatives in good yields and selectivities. We also stress the enabling triple role of tributylamine additive in this process, discuss the advantages of strategies based on proton-coupled electron transfer (PCET) and demonstrate the scale-up of this reaction in continuous flow.

The Catalyst-Controlled Divergent Cascade Reactions of Homo-Propargylic Amines and Nitrones: Synthesis of Pyrrolo-Isoxazolidines and γ-Lactams

Two controllable one-pot cascade cyclization reactions of homopropargylic amines and nitrones were developed by using different metal Cu and Ag salts. The pyrroloisoxazolidines and γ-lactams were obtained in good to high yields, respectively. Herein, nitr

Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst

Described herein is that the catalytic construction of N-substituted five- and six-membered lactams from keto acids with primary amines by reductive amination, using an indium/silane combination. This relatively benign and safe catalyst/reductant system tolerates the use of a variety of functional groups, especially ones that are reduction-sensitive. A direct switch from synthesizing lactams to synthesizing cyclic amines is achieved by changing the catalyst from In(OAc)3 to InI3. This conversion occurs by further reduction of the lactam using the indium/silane pair.

Highly efficient and versatile synthesis of lactams and N -heterocycles via Al(OTf)3-catalyzed cascade cyclization and ionic hydrogenation reactions

The discovery and development of an efficient and versatile method for the synthesis of N-substituted lactams is described. Pyrrolindinones, piperidones, and structurally related heterocycles were formed by Al(OTf)3- catalyzed cascade cyclizati

Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: V. Cyclization of anilides of styrylacetic acids in polyphosphoric acid

Anilides of styrylacetic acids at heating in polyphosphoric acid undergo an intramolecular cyclization giving 1,5-diarylpyrrolidin-2-ones, 5-aryl-1,3,4,5-tetrahydro-2H-benzazepin-2-ones, and 5-(3-fluorophenyl) dihydrofuran-2(3H)-one, where the ratio of th

Regioselective synthesis of γ-amino esters, nitriles, sulfones, and pyrrolidinones by nickel-catalyzed reductive coupling of aldimines and activated alkenes

(Chemical Equation Presented) A couple of alternatives: An efficient method has been developed for the synthesis of γ-amino derivatives and pyrrolidinones from readily available starting materials by using a nickel-phenanthroline complex (see scheme). The reaction proceeds by the formation of a C-C bond at the β-carbon atom, instead of the more usual α-carbon atom, of a conjugated alkene via an azanickelacycle intermediate.

Lactam derivatives

There is disclosed a lactam derivative of the formula: STR1 wherein R1 is a substituted or unsubstituted phenyl group; R2 is a substituted or unsubstituted phenyl group, a cycloalkyl group or a nitrogen-containing 6-membered heterocy

REACTION OF OXIRANES WITH DIANIONS OF SECONDARY AMINES. NEW ENTRY TO 5-ALKYLSUBSTITUTED γ-LACTAMS

The oxirane ring cleavage with dilithiated secondary amides was accelerated by the addition of boron trifluoride-etherate to afford γ-hydroxyamides, which were transformed into 5-alkylsubstituted γ-lactams via an intramolecular N-alkylation reaction.