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Medicinal chemistry

Papers (10)

Synthesis and Biological Evaluation of Substituted Fused Dipyranoquinolinones

Evangelia-Eirini N. Vlachou, Eleni Pontiki, Dimitra J. Hadjipavlou-Litina & Konstantinos E. Litinas · Organics · 2023

New methyl-substituted, and diphenyl-substituted fused dipyranoquinolinones are prepared in excellent yields via the triple bond activation and 6-endo-dig cyclization of propargyloxycoumarin derivatives by gold nanoparticles supported on TiO2 in chlorobenzene under microwave irra...

Open access Research Article 10.3390/org4030027

Synthesis and Wittig Rearrangement of 3- and 4-Benzyloxyphenylphosphonamidates

R. Alan Aitken & Ryan A. Inwood · Organics · 2023

A series of seven O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the para or meta position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo Wittig rearrangement in six cases to give the novel phosp...

Open access Research Article 10.3390/org4010005

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

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

Dihydrooxazine Byproduct of a McMurry–Melton Reaction en Route to a Synthetic Bacteriochlorin

Vy-Phuong Tran, Nobuyuki Matsumoto, Phattananawee Nalaoh, Haoyu Jing, Chih-Yuan Chen & Jonathan Lindsey · Organics · 2022

A synthetic route to gem-dimethyl-substituted bacteriochlorins—models of native bacteriochlorophylls—relies on the formation of a dihydrodipyrrin precursor via a series of established reactions: van Leusen pyrrole formation, Vilsmeier formylation, Henry reaction, borohydride redu...

Open access Research Article 10.3390/org3030019

Regioselective Transfer Hydrogenative Defluorination of Polyfluoroarenes Catalyzed by Bifunctional Azairidacycle

Asuka Matsunami, Shigeki Kuwata & Yoshihito Kayaki · Organics · 2022

The catalytic hydrodefluorination (HDF) with a bifunctional azairidacycle using HCOOK was examined for cyano- and chloro-substituted fluoroarenes, including penta- and tetrafluorobenzonitriles, tetrafluoroterephthalonitrile, tetrafluorophthalonitrile, 3-chloro-2,4,5,6-tetrafluoro...

Open access Research Article 10.3390/org3030012

Regioselective N- versus P-Deprotonation of Aminophosphane Tungsten(0) Complexes

Tatjana Terschüren, Philip Junker, Alexander Schmer, Arturo Espinosa Ferao & Rainer Streubel · Organics · 2022

1,2-Bifunctional ligands are rare, in general, which holds especially for those with a P-N linkage. Herein, we report on the synthesis of P-tert-butyl substituted aminophosphane W(CO)5 complexes 3a-f (a: R = R’ = H; b: R = H, R = Me; c: R = H, R’ = ally; d: R = H, R’ = i-Pr; e: R...

Open access Research Article 10.3390/org3030013

Primary Phosphines and Phosphine Oxides with a Stereogenic Carbon Center Adjacent to the Phosphorus Atom: Synthesis and Anti-Markovnikov Radical Addition to Alkenes

Toshiaki Murai, Ryota Wada, Kouji Iwata, Yuuki Maekawa, Kazuma Kuwabara & Mao Minoura · Organics · 2021

Organophosphorus compounds with stereogenic phosphorus and carbon atoms have received increasing attention. In this regards, primary phosphines with a stereogenic carbon atom adjacent to the phosphorus atom were synthesized by the reduction in phosphonates and phosphonoselenoates...

Open access Research Article 10.3390/org2040023

Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

Mohammed El Idrissi, Mohamed El Ghozlani, Asli Eşme, Mar Ríos Gutiérrez, Anas Ouled Aitouna, Mohammed Salah, Habib El Alaoui El Abdallaoui, Abdellah Zeroual, Noureddine Mazoir & Luis Domingo · Organics · 2021

The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo-4-vinylbenzene 1 and 1-chloro-4-vinylbenzene 2 with benzonitrile oxide 3 were investigated under the molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) computational level. Ev...

Open access Research Article 10.3390/org2010001