A Single-Step Synthesis of Azetidine-3-Amines

10.26434/chemrxiv.12846629 ◽

2020 ◽

Author(s):

Brian J Wang ◽

Matthew Duncton

Keyword(s):

Functional Groups ◽

Late Stage ◽

Single Step ◽

Secondary Amines ◽

High Yield ◽

Primary Amines ◽

Privileged Structure ◽

One Step ◽

Alternative Procedures ◽

Approved Drugs

<div> <p>The azetidine group is frequently encountered within contemporary medicinal chemistry where it is viewed as a privileged structure. However, the introduction of an azetidine can be synthetically challenging. Herein, a straight-forward one step synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates functional groups commonly encountered in biological-, medicinal- and agro-chemistry, and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to recent alternative procedures and can be utilized in “any-stage” functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.</p> </div>

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Efficient and mild synthesis of pyrano-pyrimidines catalyzed by decorated multi-walled carbon nanotubes bearing cobalt, nickel and copper metals in water

10.21203/rs.3.rs-932673/v1 ◽

2021 ◽

Author(s):

Nasrin Saberi Harouni ◽

Hossein Naeimi

Keyword(s):

Reaction Times ◽

Single Step ◽

High Yield ◽

One Pot ◽

H Nmr ◽

Multi Walled Carbon Nanotubes ◽

Nmr Techniques ◽

One Step ◽

Ft Ir ◽

Walled Carbon Nanotubes

Abstract Multicomponent reactions are reactions in which three or more are agreeable of raw interests, composed in a one-step chemical process and the product is formed they give. Since multivariate reactions are monovalent reactions and Single-step conversions to ideal synthesis are very close. In this research, one pot three components reaction was carried out between 1, 3-dimethylbarbituric acid, malononitrile and different aldehydes in the attendance of Cu/Co/Ni/MWCNTs as a recyclable catalyst. This catalyst indicated high catalytic actuality with good proficiency and reusable under mild reservation. This reaction is performed fine at ambient temperature. This method proposed numerous materials such as being environmentally amicable for short reaction times and creating high yield products. The catalysts were collected and specified with diversity spectroscopic, such as techniques, such as FT-IR, X-ray fracture, and scanning electron microscopy. After finalization of the reaction, the vintage was obsolete, purified and identified by the melting points, infrared spectroscopy (FT-IR) and the magnetic resonance of the hydrogen nucleus (1H NMR) techniques.

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Convenient One-Pot Four-Component Synthesis of 6,8-Disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones via a Triple Mannich Reaction

Australian Journal of Chemistry ◽

10.1071/ch19088 ◽

2019 ◽

Vol 72 (7) ◽

pp. 542 ◽

Cited By ~ 3

Author(s):

Ahmed F. M. EL-Mahdy ◽

Hassan A. H. El-Sherief ◽

Zainab A. Hozien

Keyword(s):

Reaction Mechanism ◽

Functional Groups ◽

Mannich Reaction ◽

Spectroscopic Data ◽

Atomic Charge ◽

Secondary Amines ◽

Primary Amines ◽

One Pot ◽

Elemental Analyses ◽

Charge Calculations

An efficient and simple one-pot four-component protocol has been developed and performed for the synthesis of 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones, involving a triple Mannich reaction of 6-amino-2-(ethylthio)pyrimidin-4(3H)-one, formaldehyde, primary amines, and alcohols. Secondary amines were also utilised instead of alcohols as Mannich nucleophiles, and a variety of functional groups and electronically varied reaction partners were tolerated. This one-pot reaction facilitated the generation of a library of pyrimido[4,5-d]pyrimidin-4(3H)-ones in very good to excellent yields. The regioselectivity of this reaction was investigated using atomic charge calculations, and spectroscopic data confirmed that the triple Mannich products were 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones rather than the isomeric 3,6-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones. The structures of all compounds synthesised using the triple Mannich reaction were confirmed via spectroscopic and elemental analyses. The reaction mechanism was studied and confirmed by isolation of the intermediate.

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ChemInform Abstract: Catalytic Oxidation of Secondary Amines with H2O2 over Molecular Sieves: A High Yield and Single Step Preparation of Nitrones.

ChemInform ◽

10.1002/chin.199616069 ◽

2010 ◽

Vol 27 (16) ◽

pp. no-no

Author(s):

R. JOSEPH ◽

A. SUDALAI ◽

T. RAVINDRANATHAN

Keyword(s):

Catalytic Oxidation ◽

Molecular Sieves ◽

Single Step ◽

Secondary Amines ◽

High Yield

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Catalytic Oxidation of Secondary Amines with H2O2 over Molecular Sieves: A High Yield and Single Step Preparation of Nitrones#

Synlett ◽

10.1055/s-1995-5206 ◽

1995 ◽

Vol 1995 (11) ◽

pp. 1177-1178 ◽

Cited By ~ 22

Author(s):

Reni Joseph ◽

A. Sudalai ◽

T. Ravindranathan

Keyword(s):

Catalytic Oxidation ◽

Molecular Sieves ◽

Single Step ◽

Secondary Amines ◽

High Yield

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Synthesis and Evaluation of Tetramethylguanidinium-Polyethylenimine Polymers as Efficient Gene Delivery Vectors

BioMed Research International ◽

10.1155/2014/459736 ◽

2014 ◽

Vol 2014 ◽

pp. 1-11 ◽

Cited By ~ 3

Author(s):

Manohar Mahato ◽

Santosh Yadav ◽

Pradeep Kumar ◽

Ashwani Kumar Sharma

Keyword(s):

Cell Viability ◽

Size Range ◽

Transfection Efficiency ◽

Single Step ◽

Primary Amines ◽

Gene Delivery Vectors ◽

Efficient Gene ◽

One Step ◽

Efficient Uptake ◽

Single Step Reaction

Previously, we demonstrated that 6-(N,N,N′,N′-tetramethylguanidinium chloride)-hexanoyl-polyethylenimine (THP) polymers exhibited significantly enhanced transfection efficiency and cell viability. Here, in the present study, we have synthesized a series of N,N,N′,N′-tetramethylguanidinium-polyethylenimine (TP1-TP5) polymers via a single-step reaction involving peripheral primary amines of bPEI and varying amounts of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU). These polymers were found to interact efficiently with negatively charged pDNA and formed stable complexes in the size range of ~240–450 nm. Acid-base titration profiles revealed improved buffering capacity of TP polymers as compared to bPEI. Transfection and cytotoxicity assays performed with TP/pDNA complexes on HEK293, CHO, and HeLa cells showed significantly higher transfection efficiency and cell viability with one of the complexes, TP2/pDNA complex, exhibited the highest transfection efficiency (~1.4–2.3-fold) outcompeting native bPEI and the commercially available transfection reagent, Lipofectamine 2000. Compared to previously reported THP polymers, the transfection efficiency of TP/pDNA complexes was found to be lower, as examined by flow cytometry. These results highlight the importance of the hydrophobic C-6 linker in THP polymers in forming compact nanostructures with pDNA, which might lead to efficient uptake and internalization of the complexes; however, the projected TP polymers offer an advantage of their rapid and economical one-step synthesis.

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Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate

Pure and Applied Chemistry ◽

10.1351/pac200577101719 ◽

2005 ◽

Vol 77 (10) ◽

pp. 1719-1725 ◽

Cited By ~ 24

Author(s):

Pietro Tundo ◽

Salima Bressanello ◽

Alessandro Loris ◽

Gabriel Sathicq

Keyword(s):

Aromatic Amines ◽

Dimethyl Carbonate ◽

Direct Synthesis ◽

High Yield ◽

Primary Amines ◽

Methyl Derivative ◽

Acid Base ◽

One Step ◽

Soft Acid ◽

Mechanism Of The Reaction

The mechanism of the reaction between amines with dimethyl carbonate (DMC) has been investigated. Whereas in the absence of bases, they give methylation and carboxymethylation reactions without selectivity (BAl2 and BAc2 mechanisms, respectively), in the presence of bases, the BAc2 mechanism prevails. The carbamate already formed reacts further with DMC via the BAl2 mechanism to give the corresponding N-methyl derivative. Such pronounced double selectivity has been explained in terms of Pearson's Hard-Soft Acid-Base (HSAB) theory.Accordingly, N-methylcarbamates have been prepared from primary aliphatic and aromatic amines, either at reflux temperature of DMC (90 °C) or at 230 °C in autoclave. The reaction can be carried out in one step or through the isolation of the carbamate and the subsequent methylation reaction with DMC. This method is the direct synthesis, in high yield and selectivity, of secondary N-methylamines from the corresponding primary amines.

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A simple one-step hydrothermal route towards water solubilization of carbon quantum dots from soya-nuggets for imaging applications

RSC Advances ◽

10.1039/c5ra14536h ◽

2015 ◽

Vol 5 (106) ◽

pp. 87528-87534 ◽

Cited By ~ 29

Author(s):

Prashant Dubey ◽

Kumud Malika Tripathi ◽

Ragini Mishra ◽

Anshu Bhati ◽

Anupriya Singh ◽

...

Keyword(s):

Quantum Dots ◽

Hydrothermal Process ◽

Carbon Quantum Dots ◽

Single Step ◽

Water Soluble ◽

High Yield ◽

Synthetic Approach ◽

Hydrothermal Route ◽

E Coli ◽

One Step

A high yield simple synthetic approach for water soluble photoluminescent carbon quantum dots via a single step, hydrothermal process, was described. Photoluminescent multi-colored emissions were used to label E. coli cells.

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Blends of Polyimides and Their Morphology

Eurasian Chemico-Technological Journal ◽

10.18321/ectj328 ◽

2016 ◽

Vol 6 (1) ◽

pp. 17

Author(s):

Saule Kudaikulova ◽

Galina Boiko ◽

Bulat Zhubanov ◽

N. Ashurov ◽

Sh. Sodykov ◽

...

Keyword(s):

Electron Microscopy ◽

Scanning Electron Microscopy ◽

Functional Groups ◽

Polymer Matrix ◽

Single Step ◽

Aromatic Diamines ◽

X Ray ◽

One Step ◽

Scanning Electron

The formulation of macromolecular blends on the basis of polyimides using one step catalytic polycyclocondensation is reported. Polymers with active functional groups (polyacrylamide, polycaproamide) have been suggested as catalysts for the reaction of alicyclic dianhydrides with aromatic diamines in protolytic medium. Films made from macromolecular blends of synthesized polymers have been investigated by X-ray diffractometry and scanning electron microscopy. It has been shown that single step formation of polyimide on the polymer matrix presents the possibility to prepare thin structured disperse blends in comparison with simple mixing of homopolymers.

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