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Molecules from Catalytic Processes
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Molecules from Catalytic Processes

A topical collection in Molbank (ISSN 1422-8599). This collection belongs to the section "Organic Synthesis and Biosynthesis".

Viewed by 54087

Editor

Prof. Dr. Nicola Della Ca’

E-Mail Website
Collection Editor
Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), Parco Area delle Scienze 17/A, University of Parma, 43124 Parma, PR, Italy
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 Issues, Collections and Topics in MDPI journals

Topical Collection 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.

Prof. Dr. Nicola Della Ca’
Collection Editor

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Keywords

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

Published Papers (20 papers)

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2024

Jump to: 2023, 2022, 2020, 2019, 2018

8 pages, 1433 KiB  
Short Note
Methyl 6-Benzyl-3-Hydroxy-3,6-Dimethyl-1,2-Dioxane-4-Carboxylate
by Alexandre Benech, Omar Khoumeri, Christophe Curti and Patrice Vanelle
Molbank 2024, 2024(2), M1825; https://doi.org/10.3390/M1825 - 23 May 2024
Viewed by 707
Abstract
Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale [...] Read more.
Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale synthesis, catalyzed by manganese (III) acetylacetonate, we applied the conditions previously described in the literature to one of our low-yielding asymmetrically disubstituted alkenes, (2-methylallyl)benzene. Under conditions designed for alkyl derivatives, manganese (II) and (III) acetate catalyzed its peroxycyclization with methyl 3-oxobutanoate to a 1,2-dioxane ring in the presence of oxygen from air at room temperature with a 36% yield, while an oxygen atmosphere, as described in the literature, decreased the yield to 7%. Finally, under conditions designed for aryl derivatives, the yield was reduced to 30%, showing that methylallyl derivatives have an intermediate reactivity that needs further optimization to produce 1,2-dioxane ring by manganese catalyzation in good yields. This work characterizes the product obtained and discusses the most suitable reaction conditions. Full article
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Figure 1

2023

Jump to: 2024, 2022, 2020, 2019, 2018

5 pages, 985 KiB  
Short Note
1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-trifluoromethanesulfonate
by Cosimo Cardellicchio and Maria Annunziata M. Capozzi
Molbank 2023, 2023(3), M1695; https://doi.org/10.3390/M1695 - 14 Jul 2023
Cited by 1 | Viewed by 1297
Abstract
The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield [...] Read more.
The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported. Full article
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Scheme 1

5 pages, 1067 KiB  
Short Note
3-Cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione
by Francesco Messa, Serena Perrone and Antonio Salomone
Molbank 2023, 2023(2), M1611; https://doi.org/10.3390/M1611 - 28 Mar 2023
Viewed by 1661
Abstract
The synthesis of a novel uracil derivative, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4), is reported via a four-component reaction involving an α-chloroketone (1), an aliphatic isocyanate (2), a primary aromatic amine (3) [...] Read more.
The synthesis of a novel uracil derivative, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4), is reported via a four-component reaction involving an α-chloroketone (1), an aliphatic isocyanate (2), a primary aromatic amine (3) and carbon monoxide. The proposed reaction mechanism involves a Pd-catalyzed carbonylation of 2-chloro-1-phenylethan-1-one (1), leading to a β-ketoacylpalladium key intermediate, and, at the same time, in situ formation of non-symmetrical urea deriving from cyclohexyl isocyanate (2) and p-toluidine (3). After a chemo-selective acylation of the non-symmetrical urea and the subsequent cyclization of the acylated intermediate, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4) is formed. Uracil derivative 4 was isolated in good yield (73%) and fully characterized by 1H, 13C, 2D 1H-13C HSQC and 2D 1H-13C HMBC NMR, FT-IR spectroscopy and GC-MS spectrometry. Full article
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Figure 1

2022

Jump to: 2024, 2023, 2020, 2019, 2018

4 pages, 605 KiB  
Short Note
(±)-((2S,5R)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate
by Vincenzo Piccialli
Molbank 2022, 2022(1), M1349; https://doi.org/10.3390/M1349 - 4 Mar 2022
Viewed by 2323
Abstract
In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe [...] Read more.
In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. This new derivative was fully characterised by spectroscopic methods. Full article
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Graphical abstract

2020

Jump to: 2024, 2023, 2022, 2019, 2018

11 pages, 2435 KiB  
Short Note
Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate
by Serigne Abdou Khadir Fall, Saïd Achamlale, Younas Aouine, Asmae Nakkabi, Hassane Faraj and Anouar Alami
Molbank 2020, 2020(4), M1167; https://doi.org/10.3390/M1167 - 20 Nov 2020
Cited by 2 | Viewed by 2843
Abstract
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out [...] Read more.
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis. Full article
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Figure 1

6 pages, 1025 KiB  
Communication
Catalytic Addition of Indole-2-Carboxylic Acid to 1-Hexyne
by Javier Francos, Alba E. Díaz-Álvarez and Victorio Cadierno
Molbank 2020, 2020(3), M1145; https://doi.org/10.3390/M1145 - 3 Jul 2020
Cited by 2 | Viewed by 2633
Abstract
The synthesis of two novel enol esters, namely hex-1-en-2-yl indole-2-carboxylate and hex-1-en-2-yl 1-(hex-1-en-2-yl)-indole-2-carboxylate, is presented. Both compounds were generated by addition of indole-2-carboxylic acid to 1-hexyne employing [RuCl2(η6-p-cymene)(PPh3)] and [AuCl(PPh3)]/AgPF6, respectively, as catalysts. Full article
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Figure 1

4 pages, 501 KiB  
Short Note
Dimethyl 2-(1-Methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)malonate
by Antonia Di Mola, Rosanna Filosa and Antonio Massa
Molbank 2020, 2020(2), M1124; https://doi.org/10.3390/M1124 - 6 Apr 2020
Cited by 1 | Viewed by 2576
Abstract
In this work we report a facile access to a 3,3-disubstituted isobenzofuranone by tandem addition/cyclization reaction to methyl 2-acetylbenzoate in the presence of dimethyl malonate, under basic conditions. Full article
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Graphical abstract

2019

Jump to: 2024, 2023, 2022, 2020, 2018

6 pages, 746 KiB  
Communication
(2S,5R)-2-Isopropyl-5-methylcyclohexanone Hydrazones
by Mariia Nesterkina, Dmytro Barbalat, Ivan Zheltvay, Ildar Rakipov, Mehmet Atakay, Bekir Salih and Iryna Kravchenko
Molbank 2019, 2019(2), M1062; https://doi.org/10.3390/M1062 - 29 May 2019
Cited by 6 | Viewed by 3098
Abstract
Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, [...] Read more.
Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, 1H-NMR and 13C-NMR spectral analysis and EI/FAB/ESI mass spectrometry. Thermal properties of hydrazones 3a–3e were elucidated by differential scanning calorimetry (DSC) and their purity by HPLC coupled to mass spectrometry. Synthesized compounds were found to exist as Z/E geometrical isomers about C=N bond and cis/trans amide conformers. Full article
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Graphical abstract

7 pages, 602 KiB  
Communication
4b,5,6,9-Tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin-7-one
by Maksim A. Boichenko, Igor Yu. Babkin, Sergey G. Kobylskoy, Alexey O. Chagarovskiy, Olga A. Ivanova and Igor V. Trushkov
Molbank 2019, 2019(2), M1061; https://doi.org/10.3390/M1061 - 17 May 2019
Cited by 1 | Viewed by 2606
Abstract
A simple approach to synthesize 4b,5,6,9-tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin- 7-one has been developed, based on a three-step transformation of 2-(2-bromophenyl)cyclopropane-1,1-diester. The key stage in this method is an intramolecular cross-coupling of 1-(2-bromobenzyl)-5-(2-bromophenyl)pyrrolidin-2-one under continuous flow conditions in an H-Сube-Pro using commercially available supported Pd catalysts. Full article
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Graphical abstract

5 pages, 378 KiB  
Short Note
(E)-N′-(4-Fluorobenzylidene)-5-methyl-2-(pyridin-3-yl)thiazole-4-carbohydrazide
by Vinuta Kamat, Rangappa Santosh and Suresh P. Nayak
Molbank 2019, 2019(2), M1058; https://doi.org/10.3390/M1058 - 2 May 2019
Cited by 1 | Viewed by 2396
Abstract
5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) on treatment with 4-fluorobenzaldehyde in presence of catalytic amount of acetic acid, accessed the target compound (2) with the yield of 79%. The target compound was confirmed by 1H-NMR, 13C-NMR, FT-IR and LCMS. In vitro [...] Read more.
5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) on treatment with 4-fluorobenzaldehyde in presence of catalytic amount of acetic acid, accessed the target compound (2) with the yield of 79%. The target compound was confirmed by 1H-NMR, 13C-NMR, FT-IR and LCMS. In vitro antibacterial activity against Staphylococcus aureus (S. Aureus), Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), and Pseudomonas aeruginosa (P. aeruginosa) were carried out and compound 2 showed promising activity against B. subtilis. In addition, compound 2 was analyzed for DNA binding study. It revealed that compound 2 has a promising affinity towards DNA double helix. Full article
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Scheme 1

6 pages, 1255 KiB  
Short Note
4-[(3,4-Dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
by Soukhyarani Gopal Nayak and Boja Poojary
Molbank 2019, 2019(1), M1055; https://doi.org/10.3390/M1055 - 29 Mar 2019
Viewed by 2229
Abstract
4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. [...] Read more.
4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. The obtained solid product was recrystallized from ethanol. The compound was characterized by elemental analyses, mass spectrometry, FT-IR, 1H and 13C-NMR spectroscopy. To study the binding interactions of the compound with receptor, it was docked with the human prostaglandin reductase (PTGR2). The docking pose and noncovalent interactions gave insights into its plausible inhibitory action. Full article
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Figure 1

4 pages, 446 KiB  
Short Note
9-Aminoquino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one
by Eugen Schneider and Norbert Haider
Molbank 2019, 2019(1), M1050; https://doi.org/10.3390/M1050 - 1 Mar 2019
Cited by 1 | Viewed by 2270
Abstract
Chemoselective reduction of the corresponding 9-nitro precursor by catalytic transfer hydrogenation afforded the title compound, a new 9-amino derivative of the antitumor alkaloid Luotonin A, in good yield. The structure of the compound was established by means of 1D and 2D 1H-NMR [...] Read more.
Chemoselective reduction of the corresponding 9-nitro precursor by catalytic transfer hydrogenation afforded the title compound, a new 9-amino derivative of the antitumor alkaloid Luotonin A, in good yield. The structure of the compound was established by means of 1D and 2D 1H-NMR and 13C-NMR spectroscopy as well as by EI-MS and high-resolution ESI-MS. Full article
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Graphical abstract

2018

Jump to: 2024, 2023, 2022, 2020, 2019

5 pages, 478 KiB  
Short Note
(E)-3-[3-(4-Morpholinophenyl)acryloyl]-2H-chromen-2-one
by Hery Suwito, Helda Dwi Hardiyanti, Kautsar Ul Haq, Alfinda Novi Kristanti and Miratul Khasanah
Molbank 2018, 2018(4), M1027; https://doi.org/10.3390/M1027 - 29 Oct 2018
Cited by 9 | Viewed by 2860
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
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Figure 1

5 pages, 529 KiB  
Short Note
(E)-1-(2′,4′-Dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one
by Afzal Shaik, Mahamuda Sultana Shaik and Srinivasa Babu Puttagunta
Molbank 2018, 2018(3), M1019; https://doi.org/10.3390/M1019 - 13 Sep 2018
Cited by 3 | Viewed by 3488
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
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Figure 1

4 pages, 637 KiB  
Short 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
by Dong-Jun Fu, Victor Pham, Matthew-Alexander Tippin, Liankun Song, Xiaolin Zi, En Zhang and Hong-Min Liu
Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016 - 30 Aug 2018
Viewed by 2918
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
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Figure 1

5 pages, 467 KiB  
Short Note
5-[3-(4-Bromophenyl)-1-(2,5-dimethoxyphenyl)-3-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-tri-one
by Hery Suwito, Ria Hesty Purnama Sari, Kautsar Ul Haq and Alfinda Novi Kristanti
Molbank 2018, 2018(3), M1013; https://doi.org/10.3390/M1013 - 23 Aug 2018
Viewed by 3575
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
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Figure 1

5 pages, 814 KiB  
Short Note
Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
by Hery Suwito, Noorma Kurnyawaty, Kautsar Ul Haq, Abdulloh Abdulloh and Indriani Indriani
Molbank 2018, 2018(2), M998; https://doi.org/10.3390/M998 - 28 May 2018
Cited by 3 | Viewed by 3009
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
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Figure 1

6 pages, 1153 KiB  
Short Note
1-Adamantylamidoxime
by Benjamín Diethelm, Carlos F. Lagos and Gonzalo Recabarren-Gajardo
Molbank 2018, 2018(2), M992; https://doi.org/10.3390/M992 - 19 Apr 2018
Viewed by 3372
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
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Graphical abstract

6 pages, 4383 KiB  
Short Note
Cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine
by Alessandra Casnati, Elena Motti and Nicola Della Ca’
Molbank 2018, 2018(1), M988; https://doi.org/10.3390/M988 - 12 Mar 2018
Cited by 2 | Viewed by 3206
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
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Graphical abstract

3 pages, 551 KiB  
Short Note
Dimethyl 2,2′-[Carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate]
by Raffaella Mancuso, Katia F. Gioia, Antonio Palumbo Piccionello, Nicola Della Ca’, Carla Carfagna and Bartolo Gabriele
Molbank 2018, 2018(1), M983; https://doi.org/10.3390/M983 - 19 Feb 2018
Cited by 1 | Viewed by 3103
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
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