Synthesis of 5-Amino-2-pyrrolidinone and Its Derivatives

Kosugi, Yoshiyuki; Hamaguchi, Humiko; Nagasaka, Tatsuo; Ozawa, Naganori; Ohki, Sadao

doi:10.3987/r-1980-09-1245

Cited by 17 publications

(11 citation statements)

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“…Furthermore, to demonstrate the applicability of the reaction conditions, the cyclic product ( 26 ) was synthesized using Boc‐ l ‐glutamine which required a multistep synthesis by previous chemical method [38] (Scheme 14 a). Also, they investigated the comparison experiments to check the activity of NHP ester protected N ‐Boc proline with benzimidazole under the reported photoredox conditions [36c, d] but the expected product was not observed (Scheme 14 b).…”

Section: Electrochemical Decarboxylative C−n Bond Formationmentioning

confidence: 99%

“…The solid-supported base was prepared by 0.1 m silica gel supported by piperidine in methanols olvent. The substrate scope was examined with different amino acid derivatives such as N-acylated proline ( 38), ac arbamate (39), N-acylated alanine (40), p-methoxy phenylacetic acid (41)a nd the correspondingm ethoxylated products were produced in excellent yields (Scheme 17).…”

Section: Electrochemical Decarboxylative Càob Ond Formationmentioning

confidence: 99%

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Advances in Electrochemical Decarboxylative Transformation Reactions

Ramadoss

Zheng

Shao

et al. 2020

Chemistry A European J

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Owing to their non‐toxic, stable, inexpensive properties, carboxylic acids are considered as environmentally benign alternatives as coupling partners in various organic transformations. Electrochemical mediated decarboxylation of carboxylic acid has emerged as a new and efficient methodology for the construction of carbon‐carbon or carbon‐heteroatom bonds. Compared with transition‐metal catalysis and photoredox catalysis, electro‐organic decarboxylative transformations are considered as a green and sustainable protocol due to the absence of chemical oxidants and strong bases. Further, it exhibits good tolerance with various functional groups. In this Minireview, we summarize the recent advances and discoveries on the electrochemical decarboxylative transformations on C−C and C−heteroatoms bond formations.

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Section: Electrochemical Decarboxylative C−n Bond Formationmentioning

confidence: 99%

Section: Electrochemical Decarboxylative Càob Ond Formationmentioning

confidence: 99%

Advances in Electrochemical Decarboxylative Transformation Reactions

Ramadoss

Zheng

Shao

et al. 2020

Chemistry A European J

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“…Lactams are important components of pharmaceuticals and natural products [42][43][44] and synthesis of a-, b-and g-substituted g-lactams is widely stated. Kosugi et al [45] synthesized g-Naryl-g-lactams by reacting 5-ethoxy-2-pyrrolidinone and amine in a multistep process. g-Lactam core is built by utilizing a preactivated lactam center or by intramolecular cyclization.…”

Section: Lactam Synthesismentioning

confidence: 99%

“…Lactams are important components of pharmaceuticals and natural products and synthesis of α‐, β‐ and γ‐substituted γ‐lactams is widely stated. Kosugi et al . synthesized γ‐N‐aryl‐γ‐lactams by reacting 5‐ethoxy‐2‐pyrrolidinone and amine in a multistep process.…”

Section: Coupling Chemistrymentioning

confidence: 99%

Copper Catalyzed C−H Activation

Kantam

Gadipelly

Deshmukh

et al. 2018

The Chemical Record

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Activation of C−H bonds and their application in cross coupling chemistry has received a wider interest in recent years. The conventional strategy in cross coupling reaction involves the pre‐functionalization step of coupling reactants such as organic halides, pseudo‐halides and organometallic reagents. The C−H activation facilitates a simple and straight forward approach devoid of pre‐functionalization step. This approach also addresses the environmental and economical issues involved in several chemical reactions. In this account, we have reported C−H bond activation of small organic molecules, for example, formamide C−H bond can be activated and coupled with β‐dicarbonyl or 2‐carbonyl substituted phenols under oxidative conditions to yield carbamates using inexpensive copper catalysts. Phenyl carbamates were successfully synthesized in moderate to good yields by cross dehydrogenative coupling (CDC) of phenols with formamides using copper catalysts in presence of a ligand. We have also prepared unsymmetrical urea derivatives by oxidative cross coupling of formamides with amines using copper catalysts. Synthesis of N,N‐dimethyl substituted amides, 5‐substituted‐γ‐lactams and α‐acyloxy ethers was carried out from carboxylic acids using recyclable CuO nanoparticles. Copper nanoparticles afforded N‐aryl‐γ‐amino‐γ‐lactams by oxidative coupling of aromatic amines with 2‐pyrrolidinone. Reusable transition metal HT‐derived oxide catalyst was used for the synthesis of N,N‐dimethyl substituted amides by the oxidative cross‐coupling of carboxylic acids and substituted benzaldehydes. Overview of our work in this area is summarized.

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“…The 5-aminopyrrolidin-2-one 1 motif (or γ-amino-γ-lactam) 1, belonging to the cyclic N,N-acetal family, is encountered in numerous unnatural compounds with a wide range of biological applications. These compounds, which are typically produced by Curtius-type rearrangement of pyroglutamic acid derivatives including amides 2 or carbamates, 3 have been used for the synthesis of retro-inverso peptides of type 2 (Y = NH) 3 or 3 (Y = CO) 4 (Figure 1). These classes of products containing a cyclic N,N-acetal, exemplified by compounds 4, 5 5 6 and 6, 7 display antidepressant, 6 antihypertensive and cardiovascular activities.…”

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confidence: 99%

Triflic Acid Catalyzed Intermolecular α-Amination of Pterolactams To Give 5-Arylaminopyrrolidinones via N-Acyliminium Species

Dumitriu

Bîcu

Eryuruk

et al. 2016

Synlett

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Starting materials are commercially available. Melting points were measured on an MPA 100 OptiMelt® apparatus and are uncorrected. NMR spectra were acquired at 200 MHz for 1 H NMR on a Varian Gemini 2000® spectrometer, or at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR on a Varian 400 MHz Premium Shielded® spectrometer. Chemical shifts (δ) are expressed in parts per million relative to TMS as internal standard. Thin layer chromatography (TLC) was realized on Macherey Nagel silica gel plates with fluorescent indicator and was visualized under a UV-lamp at 254 nm and 366 nm. Column chromatography was performed on silica gel (40-60 µm; Macherey Nagel). IR spectra were recorded on a Varian 640-IR FT-IR Spectrometer. Elemental analysis (C, H, N, S) of new compounds was determined

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Synthesis of 5-Amino-2-pyrrolidinone and Its Derivatives

Cited by 17 publications

References 0 publications

Advances in Electrochemical Decarboxylative Transformation Reactions

Advances in Electrochemical Decarboxylative Transformation Reactions

Copper Catalyzed C−H Activation

Triflic Acid Catalyzed Intermolecular α-Amination of Pterolactams To Give 5-Arylaminopyrrolidinones via N-Acyliminium Species

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