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Special Issue "Molecules from Catalytic Processes"

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: 31 August 2019

Special Issue Editor

Guest Editor
Dr. Nicola Della Ca'

Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), Parco Area delle Scienze 17/A, University of Parma, 43124—Parma (PR), Italy
Website | E-Mail
Interests: catalytic sequential reactions for the synthesis of high value-added compounds from readily available reagents, transition metal-catalyzed C-H activation methodologies, carbonylation reactions, CO2 activation chemistry

Special Issue Information

Dear Colleagues,

Catalytic reactions represent an outstanding tool to access structurally-complex molecules of relevant interest for academia and industry. Often, sequential catalytic transformations lead to a high level of molecular sophistication that is hard to reach through the traditional organic chemistry. The use of readily available starting materials avoiding at the same time tedious separation steps increases the synthetic importance and the potentiality of these catalytic processes. The focus of this Special Issue is to present papers that cover the synthesis of a single compound or a family of molecules through a catalytic transformation, including metal- or organocatalyzed syntheses. All contributions on this topic are encouraged.

Dr. Nicola Della Ca'
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molbank is an international peer-reviewed open access quarterly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 350 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • catalytic processes
  • metal-catalyzed organic synthesis
  • organocatalyzed transformations
  • high-value added molecules
  • heterocycle synthesis

Published Papers (8 papers)

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Research

Open AccessShort Note (E)-3-[3-(4-Morpholinophenyl)acryloyl]-2H-chromen-2-one
Molbank 2018, 2018(4), M1027; https://doi.org/10.3390/M1027
Received: 23 September 2018 / Revised: 21 October 2018 / Accepted: 25 October 2018 / Published: 29 October 2018
PDF Full-text (478 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the
[...] Read more.
A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, 1H- and 13C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note (E)-1-(2′,4′-Dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one
Molbank 2018, 2018(3), M1019; https://doi.org/10.3390/M1019
Received: 27 August 2018 / Revised: 10 September 2018 / Accepted: 12 September 2018 / Published: 13 September 2018
PDF Full-text (529 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was
[...] Read more.
Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was synthesized by the acid-catalyzed condensation of 2,4-dimethyl-5-acetylthiazole with 2,4-difluorobenzaldehyde. Purification and characterization of the compound were carried out by recrystallization and spectral techniques including UV, IR, 1H-NMR, 13C-NMR, Mass spectrometry and X-ray powdered diffractometry. The molecule 3c was successfully synthesized, purified, and characterized. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note (1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one
Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016
Received: 11 August 2018 / Revised: 25 August 2018 / Accepted: 28 August 2018 / Published: 30 August 2018
PDF Full-text (637 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS
[...] Read more.
Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS in this work. It is worth noting that compound 9 is an entirely new compound. Additionally, a plausible mechanism and effects on the formation of 9 by different Lewis acids were proposed. The discovery of compound 9 could improve the purity of this feasible industrial synthesis and provide considerable cost savings. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note 5-[3-(4-Bromophenyl)-1-(2,5-dimethoxyphenyl)-3-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-tri-one
Molbank 2018, 2018(3), M1013; https://doi.org/10.3390/M1013
Received: 2 August 2018 / Revised: 19 August 2018 / Accepted: 20 August 2018 / Published: 23 August 2018
PDF Full-text (467 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was
[...] Read more.
The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was established by spectral data: FTIR, HRESIMS, 1H- and 13C-NMR. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
Molbank 2018, 2018(2), M998; https://doi.org/10.3390/M998
Received: 8 May 2018 / Revised: 24 May 2018 / Accepted: 24 May 2018 / Published: 28 May 2018
Cited by 1 | PDF Full-text (814 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular
[...] Read more.
A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular structure of the title compound was characterized on the basis of spectroscopic evidence, using FTIR, HRESI-MS, 1H- and 13C-NMR, and 2D NMR. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note 1-Adamantylamidoxime
Molbank 2018, 2018(2), M992; https://doi.org/10.3390/M992
Received: 6 April 2018 / Revised: 13 April 2018 / Accepted: 17 April 2018 / Published: 19 April 2018
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Abstract
The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation
[...] Read more.
The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation did not lead to product formation. Therefore, Lewis acid catalysis was attempted. Initial tests with ZnCl2 led to product formation in poor yields. Conversely, the use of AlCl3 led to the formation of the desired amidoxime in the moderate yield, which was further increased to an excellent yield by performing the reaction in a more concentrated medium. The structural identity of the title compound was proven by spectroscopic methods (IR, NMR). This compound was later employed as a starting material for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives as potential 11β-HSD1 inhibitors. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Figures

Graphical abstract

Open AccessShort Note Cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine
Molbank 2018, 2018(1), M988; https://doi.org/10.3390/M988
Received: 20 February 2018 / Revised: 9 March 2018 / Accepted: 10 March 2018 / Published: 12 March 2018
PDF Full-text (4383 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine derivative was fully characterized (FT-IR, MS, 1H and 13C-NMR, elemental analysis)
[...] Read more.
The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine derivative was fully characterized (FT-IR, MS, 1H and 13C-NMR, elemental analysis) and all proton and carbon signals have been completely assigned by 2D NMR experiments. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Figures

Graphical abstract

Open AccessFeature PaperShort Note Dimethyl 2,2′-[Carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate]
Molbank 2018, 2018(1), M983; https://doi.org/10.3390/M983
Received: 30 January 2018 / Revised: 14 February 2018 / Accepted: 16 February 2018 / Published: 19 February 2018
PDF Full-text (551 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The thus-far unknown ureic derivative dimethyl 2,2′-[carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate] has been efficiently synthesized by enantiospecific oxidative carbonylation of readily available l-tyrosine methyl ester, using a very simple catalytic system (PdI2 in conjunction with KI) under relatively mild conditions (100 °C
[...] Read more.
The thus-far unknown ureic derivative dimethyl 2,2′-[carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate] has been efficiently synthesized by enantiospecific oxidative carbonylation of readily available l-tyrosine methyl ester, using a very simple catalytic system (PdI2 in conjunction with KI) under relatively mild conditions (100 °C for 5 h in DME as the solvent and under 20 atm of a 4:1 mixture CO-air). Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Figures

Graphical abstract

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