scholarly journals One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

2015 ◽  
Vol 13 (34) ◽  
pp. 8993-8995 ◽  
Author(s):  
Vladimir A. Maslivetc ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
One Pot Synthesis ◽  
Primary And Secondary Amines ◽  
Donor Acceptor

A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.

scholarly journals Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes

Synthesis ◽  
2019 ◽  
Vol 52 (08) ◽  
pp. 1247-1252 ◽  
Author(s):  
Sumin Lee ◽  
Young Jin Jang ◽  
Erik J. T. Phipps ◽  
Honghui Lei ◽  
Tomislav Rovis
Keyword(s):  
Good Yield ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
Rapid Access ◽  
Primary And Secondary Amines ◽  
Terminal Alkenes ◽  
Broad Array ◽  
Vicinal Diamines

We report a three-component diamination of simple unactivated alkenes using an electrophilic nitrene source and amine nucleo­philes. The reaction provides rapid access to 1,2-vicinal diamines from terminal alkenes through a one-pot protocol. The transformation proceeds smoothly with excellent tolerance for a broad array of primary and secondary amines, affording the desired products in good yield and regioselectivity. The mechanism is proposed to proceed through a Rh(III)-catalyzed aziridination of alkenes with subsequent ring opening by primary or secondary amines.

scholarly journals Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3700
Author(s):  
Yu Zhao ◽  
Zitong Zhou ◽  
Man Chen ◽  
Weiguang Yang
Keyword(s):  
Nucleophilic Addition ◽  
Ring Opening ◽  
Room Temperature ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Sulfonyl Azides ◽  
The Stability

N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

scholarly journals Straightforward One-Pot Syntheses of Silylamides of Magnesium and Calcium via an In Situ Grignard Metalation Method

Synthesis ◽  
2018 ◽  
Vol 51 (05) ◽  
pp. 1115-1122 ◽  
Author(s):  
Sven Krieck ◽  
Philipp Schüler ◽  
Jan Peschel ◽  
Matthias Westerhausen
Keyword(s):  
Large Scale ◽  
Room Temperature ◽  
Secondary Amines ◽  
Complex Calcium ◽  
One Pot ◽  
Primary And Secondary Amines ◽  
Catalytic Applications

Calcium bis[bis(trimethylsilyl)amide] (Ca(HMDS)2) is a widely used reagent in diverse stoichiometric and catalytic applications. These processes necessitate a straightforward and large-scale access of this complex. Calcium does not react with primary and secondary amines, but the addition of excess bromoethane to a mixture of calcium turnings and amines in THF at room temperature yields the corresponding calcium bis(amides), calcium bromide and ethane. This in situ Grignard metalation method (iGMM) allows the preparation of calcium bis(amides) from secondary and primary trialkylsilyl-substituted amines and anilines on a multigram scale.1 Background2 The In Situ Grignard Metalation Method (iGMM)3 Properties of [(thf)2M(HMDS)2]4 Applications and Perspective

Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C–H activation

RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89413-89416 ◽  
Author(s):  
Jiajia Gu ◽  
Zheng Fang ◽  
Yuhang Yang ◽  
Zhao Yang ◽  
Li Wan ◽  
...  
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Mild Conditions ◽  
Primary And Secondary Amines ◽  
Aromatic Alcohols ◽  
Oxidative Amidation

Copper-catalyzed one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, to form amides under mild conditions.

An Overview of the One-pot Synthesis of Imidazolines

2020 ◽  
Vol 24 (20) ◽  
pp. 2341-2355
Author(s):  
Thaipparambil Aneeja ◽  
Sankaran Radhika ◽  
Mohan Neetha ◽  
Gopinathan Anilkumar
Keyword(s):  
Asymmetric Catalysis ◽  
Organic Compounds ◽  
Ring Opening ◽  
Ecological Impact ◽  
Chiral Auxiliary ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Synthetic Intermediate ◽  
Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

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