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All published articles 212

Exploring the Limits of Reactivity of N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Disubstituted Bicycloalkadienes in the Homo-Diels–Alder Reaction

Gary W. Breton & Kenneth L. Martin · Organics · 2022

The [2+2+2] cycloaddition (homo-Diels–Alder reaction) of N-substituted 1,2,4-triazoline-3,5-diones (TADs) with bicycloalkadienes produces strained heterocyclic compounds. A reaction with the unsubstituted dienes occurs readily to produce only the expected homo-Diels–Alder adducts...

Open access Research Article 10.3390/org4010002

Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis

Ravi Varala, Vittal Seema & Narsimhaswamy Dubasi · Organics · 2022

One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented repr...

Open access Research Article 10.3390/org4010001

Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide

Hiroki Tanimoto, Ryo Adachi, Aoi Otsuki & Takenori Tomohiro · Organics · 2022

We studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless...

Open access Research Article 10.3390/org3040035

Efficient Synthesis of a 2-Decyl-tetradecyl Substituted 7-Bromophenothiazine-3-carbaldehyde Building Block for Functional Dyes

Burak Kürsat Börüsah & Thomas J. J. Müller · Organics · 2022

(1) Polyfunctional molecules are versatile building blocks for efficient syntheses of novel phenothiazine-based materials with promising electronic properties. A prerequisite is a facile, high yielding access to these building blocks that bear solubilizing moieties and functional...

Open access Research Article 10.3390/org3040033

Phosphonated Polyethylenimine Maghemite Nanoparticles: A Convenient Support of Palladium for Cross-Coupling Reactions

Clément Monteil, Etienne Jean, Nathalie Bar & Didier Villemin · Organics · 2022

Phosphonated polyethylenimine grafted on iron oxide nanoparticles was used as a magnetic support for loading palladium. This cheap and accessible heterogeneous catalyst demonstrated good efficiency in Suzuki-Miyaura, Mizoroki-Heck, and Tsuji-Trost couplings. The nanocomposite is...

Open access Research Article 10.3390/org3040032

Synthesis of 3-Hydroxy-9H-fluorene-2-carboxylates via Michael Reaction, Robinson Annulation, and Aromatization

Yu-Min Wang, Yi-Hung Liu & Shiuh-Tzung Liu · Organics · 2022

A series of 3-hydroxy-fluorene-2-carboxylate compounds were prepared from Michael addition of acetoacetate to 2-benzylideneindan-l-one followed by Robinson annulation and aromatization. In this reaction, we were able to isolate two Robinson annulation products and characterize th...

Open access Research Article 10.3390/org3040031

How Do Positions of Phosphito Units on a Calix[4]Arene Platform Affect the Enantioselectivity of a Catalytic Reaction?

Shaima Hkiri & David Sémeril · Organics · 2022

Three chiral diphosphites, (S,S)-5,17-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy)-25,26,27,28-tetrapropyloxycalix[4]arene (1), (S,S)-5,11,17,23-tetra-tert-butyl-25,27-dipropoxy-26,28-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy)calix[4]arene (2) and (S,S)-5,11,17,23-tetra-tert-bu...

Open access Research Article 10.3390/org3040030

Thienothiophene Scaffolds as Building Blocks for (Opto)Electronics

Jan Podlesný & Filip Bureš · Organics · 2022

Thieno[3,2-b]thiophene and isomeric thieno[2,3-b]thiophene represent fused, bicyclic and electron rich heterocycles. These small planar organic compounds belong to the remarkable family of annulated building blocks for various organic materials. The first part of this review focu...

Open access Research Article 10.3390/org3040029

Synthetic Pathways to Pyrido[3,4-c]pyridazines and Their Polycyclic Derivatives

Temitayo Omowumi Alegbejo Price, Flavio Emery & Wim Dehaen · Organics · 2022

Pyrido[3,4-c]pyridazines are nitrogen-containing scaffolds that have been described as being promising in medicinal chemistry, but they are rather rare chemicals. In this review article, the literature on synthetic pathways towards pyrido[3,4-c]pyridazines is listed exhaustively,...

Open access Research Article 10.3390/org3040028

Design, Synthesis, and Photo-Responsive Properties of a Collagen Model Peptide Bearing an Azobenzene

Daisuke Sato, Hitomi Goto, Yui Ishizaki, Tetsuya Narimatsu & Tamaki Kato · Organics · 2022

Collagen is a vital component of the extracellular matrix in animals. Collagen forms a characteristic triple helical structure and plays a key role in supporting connective tissues and cell adhesion. The ability to control the collagen triple helix structure is useful for medical...

Open access Research Article 10.3390/org3040027

Ten Years Milestones in Xanthine Oxidase Inhibitors Discovery: Febuxostat-Based Inhibitors Trends, Bifunctional Derivatives, and Automatized Screening Assays

Miguel F. S. de Abreu, Camila A. Wegermann, Millena S. Ceroullo, Isabella G. M. Sant’Anna & Renato C. S. Lessa · Organics · 2022

Xanthine oxidase (XO) is an enzyme involved in the oxidative process of hypoxanthine and xanthine to uric acid (UA). This process also produces reactive oxygen species (ROS) as byproducts. Both UA and ROS are dangerous for human health, and some health conditions trigger upregula...

Open access Research Article 10.3390/org3040026

Total Syntheses of Chloropupukeananin and Its Related Natural Products

Takahiro Suzuki · Organics · 2022

Chloropupukeananin is a natural product that inhibits HIV-1 replication and has antitumor activity. Its structure consists of a chlorinated tricyclo[4.3.1.03,7]decane core skeleton with an array of highly oxidized multifunctional groups. In the biosynthesis of chloropupukeananin,...

Open access Research Article 10.3390/org3030023

Divergent Synthesis of Four Monomeric Ellagitannins toward the Total Synthesis of an Oligomeric Ellagitannin, Nobotanin K

Hajime Hashimoto, Shinnosuke Wakamori, Kazutada Ikeuchi & Hidetoshi Yamada · Organics · 2022

Oligomeric ellagitannins are challenging synthetic targets due to the need for an abundant supply of their composed monomeric ellagitannins and a synthetic methodology to connect them. This work focused on the divergent synthesis of the four monomeric ellagitannins from a common...

Open access Research Article 10.3390/org3030022

Unveiling the Origin of the Selectivity and the Molecular Mechanism in the [3+2] Cycloaddition Reaction of N-aryl-C-carbamoylnitrone with N-arylitaconimide

Abdelmalek Khorief Nacereddine & Fouad Chafaa · Organics · 2022

The [3+2] cycloaddition reaction of N-aryl-C-carbamoylnitrone (nitrone 1) with N-arylitaconimide (ethylene 2) was computationally studied using the B3LYP/6-31G(d) level of theory. An analysis of the different energetic profiles and the transition states’ optimized structures clea...

Open access Research Article 10.3390/org3030021