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Advances in One-Pot Reaction
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Advances in One-Pot Reaction

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 January 2020) | Viewed by 16182

Special Issue Editor

Prof. Dr. Romano V. A. Orru

E-Mail Website
Guest Editor
Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
Interests: synthetic methodology; multi component reactions; biocatalysis; natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

One-pot cascade reactions (processes comprising several consecutive reactions) allow scientists to carry out chemical syntheses to completion in fewer steps than conventional techniques. Generally, they improve the eco-friendliness and time-cost efficiency associated with the synthesis of drugs and other high-value organic molecules. Therefore, these one-pot processes have the potential to reduce our environmental impact, and lower the overall costs associated with producing life-saving medicines. Developing more efficient techniques for synthesising complex drug molecules like for example heterocycles or peptide mimics is a painstaking process. Working towards higher efficiency and yield in the synthesis of pharmaceutical drugs using one-pot reactions in order to improve accessibility to life-saving medicines is at the heart of this Special Issue of Molecules. 

Prof. Romano V. A. Orru
Guest Editor

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Keywords

  • One-pot processes
  • Green chemistry
  • Cascade reactions
  • Biocatalysis
  • Atom- and Step efficiency
  • Organic Synthesis

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Published Papers (4 papers)

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Research

11 pages, 2725 KiB  
Article
Hf(OTf)4 as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
by Shuai-Bo Han, Jing-Ying Wei, Xiao-Chong Peng, Rong Liu, Shan-Shan Gong and Qi Sun
Molecules 2020, 25(2), 388; https://doi.org/10.3390/molecules25020388 - 17 Jan 2020
Cited by 9 | Viewed by 3111
Abstract
Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange [...] Read more.
Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the keto-enol tautomerization, thereby contributing to the acceleration of reaction rate. Full article
(This article belongs to the Special Issue Advances in One-Pot Reaction)
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10 pages, 899 KiB  
Article
New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study
by Eva Havránková, Jozef Csöllei and Pavel Pazdera
Molecules 2019, 24(19), 3586; https://doi.org/10.3390/molecules24193586 - 5 Oct 2019
Cited by 14 | Viewed by 2854
Abstract
An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The [...] Read more.
An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type reactions provide significantly shortened reaction times and, in some cases, also higher yields. Finally, trisubstituted s-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new s-triazine derivatives with potential biological activity were prepared and characterized. Full article
(This article belongs to the Special Issue Advances in One-Pot Reaction)
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13 pages, 1270 KiB  
Communication
An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
by Wengang Wu, Jun Yi, Huipeng Xu, Shuangjun Li and Rongxin Yuan
Molecules 2019, 24(7), 1234; https://doi.org/10.3390/molecules24071234 - 29 Mar 2019
Cited by 8 | Viewed by 4186
Abstract
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of [...] Read more.
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields. Full article
(This article belongs to the Special Issue Advances in One-Pot Reaction)
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14 pages, 2197 KiB  
Article
Highly Efficient Synthesis of Substituted 3,4-Dihydropyrimidin-2-(1H)-ones (DHPMs) Catalyzed by Hf(OTf)4: Mechanistic Insights into Reaction Pathways under Metal Lewis Acid Catalysis and Solvent-Free Conditions
by Rui Kong, Shuai-Bo Han, Jing-Ying Wei, Xiao-Chong Peng, Zhen-Biao Xie, Shan-Shan Gong and Qi Sun
Molecules 2019, 24(2), 364; https://doi.org/10.3390/molecules24020364 - 21 Jan 2019
Cited by 32 | Viewed by 5196
Abstract
In our studies on the catalytic activity of Group IVB transition metal Lewis acids, Hf(OTf)4 was identified as a highly potent catalyst for ”one-pot, three-component” Biginelli reaction. More importantly, it was found that solvent-free conditions, in contrast to solvent-based conditions, could dramatically [...] Read more.
In our studies on the catalytic activity of Group IVB transition metal Lewis acids, Hf(OTf)4 was identified as a highly potent catalyst for ”one-pot, three-component” Biginelli reaction. More importantly, it was found that solvent-free conditions, in contrast to solvent-based conditions, could dramatically promote the Hf(OTf)4-catalyzed formation of 3,4-dihydro-pyrimidin-2-(1H)-ones. To provide a mechanistic explanation, we closely examined the catalytic effects of Hf(OTf)4 on all three potential reaction pathways in both “sequential bimolecular condensations” and “one-pot, three-component” manners. The experimental results showed that the synergistic effects of solvent-free conditions and Hf(OTf)4 catalysis not only drastically accelerate Biginelli reaction by enhancing the imine route and activating the enamine route but also avoid the formation of Knoevenagel adduct, which may lead to an undesired byproduct. In addition, 1H-MMR tracing of the H-D exchange reaction of methyl acetoacetate in MeOH-d4 indicated that Hf(IV) cation may significantly accelerate ketone-enol tautomerization and activate the β-ketone moiety, thereby contributing to the overall reaction rate. Full article
(This article belongs to the Special Issue Advances in One-Pot Reaction)
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