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Recent Advances in Cascade Reactions and Related One-Pot Processes

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

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 18050

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Special Issue Editor

Dr. Antonio Massa

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Guest Editor

Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, SA, Italy
Interests: synthetic methodologies; asymmetric catalysis; total synthesis; heterocycles; biologically active compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The interest of the chemical community in “one-pot” reactions has increased considerably over the past two decades. These processes, which also include cascade, tandem, and domino reactions, are characterized by a high level of atom and step economy. Even though some mechanistic distinctions have been proposed in the pioneering works reported by Tietze, Enders, Fogg, and dos Santos, as of more recently, these three terms have been used interchangeably and generally refer to a process involving two or more consecutive reactions in which subsequent reactions result as a consequence of the functionality formed in the previous step, without the isolation of the intermediates.

A successful one-pot or cascade reaction should include several aspects, such as a wide substrate scope, a benign work-up process, and the possibility of cost-effective scale-up, as well as the potential to develop catalytic asymmetric versions wherein new stereocenters are formed. Therefore, applications of asymmetric catalysis in one-pot methodologies for the total synthesis of bioactive compounds are subjects of high interest for this Special Issue. The development of new cascade reactions is strongly related to the rational design of multifunctional substrates. The synthesis of these compounds can be complicated, and therefore can be a genuine limitation for the entire process. For these reasons, we encourage the focus on mechanistic investigations aimed toward the comprehension of all the aspects of these complex reactions and to predict new transformations, as well as on the development of effective synthetic strategies of the starting materials.

Within the scope of this Special Issue, we welcome full and mini-reviews, original research articles, and method articles.

Prof. Antonio Massa
Guest Editor

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Keywords

Design, synthesis, and transformations of multifunctional molecules
Catalytic asymmetric one-pot reactions
Multicomponent reactions
Organocatalytic domino transformations
Applications in total synthesis of natural products and pharmacologically active compounds
Scale-up and sustainable synthesis
Mechanistic investigations

Published Papers (7 papers)

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Research

13 pages, 3274 KiB

Open AccessArticle

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

by Shrikant G. Pharande, Manuel A. Rentería-Gómez and Rocío Gámez-Montaño

Molecules 2020, 25(22), 5246; https://doi.org/10.3390/molecules25225246 - 11 Nov 2020

Cited by 6 | Viewed by 2223

Abstract

A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20–55%. This strategy allows the construction of six heterocycles in two stages of the reaction. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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Graphical abstract

17 pages, 3584 KiB

Open AccessArticle

Naphthalenes and Quinolines by Domino Reactions of Morita–Baylis–Hillman Acetates

by Joel K. Annor-Gyamfi, Ebenezer Ametsetor, Kevin Meraz and Richard A. Bunce

Molecules 2020, 25(21), 5168; https://doi.org/10.3390/molecules25215168 - 6 Nov 2020

Cited by 4 | Viewed by 1968

Abstract

An efficient synthetic route to highly functionalized naphthalenes and quinolines has been developed using domino reactions between Morita–Baylis–Hillman (MBH) acetates and active methylene compounds (AMCs) promoted by anhydrous K₂CO₃ in dry N,N-dimethylformamide (DMF) at 23 °C. The substrates incorporate allylic acetates positioned adjacent to a Michael acceptor as well as an aromatic ring activated toward a S_NAr ring closure. A control experiment indicated that the initial reaction was an S_N2’-type displacement of a side chain acetoxy by the AMC anion to afford the alkene product bearing the added nucleophile trans to the S_NAr aromatic ring acceptor. Thus, equilibration of the alkene geometry of the initial product was required prior to cyclization. Products were isolated in good to excellent yields. Numerous cases (24) are reported, and several mechanistic possibilities are discussed. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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Graphical abstract

11 pages, 5963 KiB

Open AccessArticle

A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-c]pyran-1-ones, Indolo[3,2-c]pyran-1-ones, Thieno[2,3-c]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-a]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction

by Badr Jismy, Khalil Cherry, Carine Maaliki, Samuel Inack Ngi and Mohamed Abarbri

Molecules 2020, 25(21), 5137; https://doi.org/10.3390/molecules25215137 - 4 Nov 2020

Cited by 2 | Viewed by 2163

Abstract

A general regioselective one-pot synthesis of 1,2-benzothiazine 1,1-dioxides from 2-iodo benzenesulfonamide moieties and allenylstannanes is described using a domino Stille-like/Azacyclization reaction. The conditions developed also opened a novel access to β-carbolinones, indolopyranones, thienopyranones and pyrano-imidazopyridines. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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9 pages, 1082 KiB

Open AccessArticle

[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids

by Raju Suresh Kumar, Dhaifallah M. Al-thamili, Abdulrahman I. Almansour, Natarajan Arumugam and Necmi Dege

Molecules 2020, 25(20), 4779; https://doi.org/10.3390/molecules25204779 - 18 Oct 2020

Cited by 5 | Viewed by 1921

Abstract

Our synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones and azomethine ylide generated in situ from isatin and L-phenyl alanine, affording a series of spirooxindole–pyrrolidine heterocyclic hybrids in good-to-excellent yields. In addition to serving as the reaction medium, [bmim]Br also functioned as a catalyst in this cycloaddition reaction and hence accelerated the reaction rate affording the cycloadducts in short reaction time. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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Graphical abstract

9 pages, 1751 KiB

Open AccessArticle

Development of One Pot Strategy for Hyper Production and In Vivo Evaluation of Lovastatin

by Muhammad Azeem, Muhammad Arshad, Saqib Mahmood, Shazia Abrar, Ameer Fawad Zahoor, Sadia Javed, Bisma Tariq and Khizar Hayyat

Molecules 2020, 25(19), 4380; https://doi.org/10.3390/molecules25194380 - 24 Sep 2020

Cited by 4 | Viewed by 2381

Abstract

The aim of this project was to improve the Aspergillus terreus strain and pretreatment of sugarcane bagasse as carrier substrate for bulk production of lovastatin, a cholesterol-lowering drug, in solid state fermentation. Sugarcane bagasse was treated with alkali (1–3% NaOH) for the conversion of complex polysaccharides into simple sugars for better utilization of carrier substrate by microorganism for maximum lovastatin production. Ethidium bromide (time of exposure 30–180 min) was used to induce mutation in Aspergillus terreus and the best mutant was selected on the basis of inhibition zone appeared on petri plates. Fermented lovastatin was quantified by high-performance liquid chromatography. The fermented lovastatin, produced by parent and mutant Aspergillus terreus strain, was checked on body weight, blood glucose and serum cholesterol, ALT, AST, HDL-C, LDL-C, TG and TC levels of rats for their cholesterol lowering capacity. Our results indicate that selected strain along with 2% NaOH treated sugar cane bagasse was best suitable for bulk production of lovastatin by fermentation and fermented lovastatin effectively lower the cholesterol level of rats. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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Graphical abstract

10 pages, 1699 KiB

Open AccessFeature PaperArticle

Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

by Antonia Di Mola, Consiglia Tedesco and Antonio Massa

Molecules 2019, 24(11), 2177; https://doi.org/10.3390/molecules24112177 - 10 Jun 2019

Cited by 5 | Viewed by 3061

Abstract

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to a series of isoquinoline-1,3,4(2H)-triones, a class of heterocyclic compounds of great interest containing an oxygen-rich heterocyclic scaffold. A modification of the original protocol, utilizing a Staudinger reaction in the presence of trimethylphosphine, was necessary for the synthesis of Caspase inhibitor trione with free NH group. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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Graphical abstract

10 pages, 7556 KiB

Open AccessArticle

The Role Ionic Liquid [BMIM][PF₆] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction

by Poliane K. Batista, João Marcos G. de O. Ferreira, Fabio P. L. Silva, Mario L. A. A Vasconcellos and Juliana A. Vale

Molecules 2019, 24(11), 2084; https://doi.org/10.3390/molecules24112084 - 31 May 2019

Cited by 5 | Viewed by 3737

Abstract

Tetrahydropyran (THP) rings are common in several natural products, therefore, various strategies are being developed to synthesize these rings. The present work described the study of a one-pot synthesis of 2,4,6-trisubstituted tetrahydropyran compounds promoted by the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF₆] through a Barbier–Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF₆] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF₆-, accelerates the Barbier reaction when used alone, and the excess SnBr₂ from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic liquid can be recovered and reused five times in the preparation of 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran without significant yield loss. Full article

(This article belongs to the Special Issue Recent Advances in Cascade Reactions and Related One-Pot Processes)

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