Literature DB >> 25558982

Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Andrii Monastyrskyi1, Niranjan K Namelikonda1, Roman Manetsch1.   

Abstract

A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.

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Year:  2015        PMID： 25558982      PMCID： PMC4479256          DOI： 10.1021/jo5023958

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  37 in total

1.  Alpha-arylation by rearrangement: on the reaction of enolates with diaryliodonium salts.

Authors:  Per-Ola Norrby; Tue B Petersen; Marcin Bielawski; Berit Olofsson
Journal:  Chemistry       Date:  2010-07-26       Impact factor: 5.236

2.  New series of antiprion compounds: pyrazolone derivatives have the potent activity of inhibiting protease-resistant prion protein accumulation.

Authors:  Ayako Kimata; Hidehiko Nakagawa; Ryo Ohyama; Tomoko Fukuuchi; Shigeru Ohta; Katsumi Doh-ura; Takayoshi Suzuki; Naoki Miyata
Journal:  J Med Chem       Date:  2007-09-13       Impact factor: 7.446

3.  3-Aryl-4-methyl-2-quinolones targeting multiresistant Staphylococcus aureus bacteria.

Authors:  Anne Doléans-Jordheim; Jean-Baptiste Veron; Olivier Fendrich; Emmanuelle Bergeron; Adrien Montagut-Romans; Yung-Sing Wong; Bianca Furdui; Jean Freney; Charles Dumontet; Ahcène Boumendjel
Journal:  ChemMedChem       Date:  2013-02-21       Impact factor: 3.466

4.  Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts.

Authors:  Nazli Jalalian; Eloisa E Ishikawa; Luiz F Silva; Berit Olofsson
Journal:  Org Lett       Date:  2011-02-14       Impact factor: 6.005

5.  Palladium-catalyzed C-H arylation of 2,5-substituted pyrroles.

Authors:  Anna M Wagner; Melanie S Sanford
Journal:  Org Lett       Date:  2010-12-08       Impact factor: 6.005

6.  CuI-catalyzed domino process to 2,3-disubstituted benzofurans from 1-bromo-2-iodobenzenes and beta-keto esters.

Authors:  Biao Lu; Bao Wang; Yihua Zhang; Dawei Ma
Journal:  J Org Chem       Date:  2007-06-19       Impact factor: 4.354

7.  Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate.

Authors:  Gui-Rong Qu; Zhi-Jie Mao; Hong-Ying Niu; Dong-Chao Wang; Chao Xia; Hai-Ming Guo
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

8.  Solution and crystal lattice effects on the photochemistry of 6-substituted cyclohexenones(1)(,)(2).

Authors:  Howard E Zimmerman; Grigoriy A Sereda
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

9.  Diaryliodonium salts: a journey from obscurity to fame.

Authors:  Eleanor A Merritt; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Orally bioavailable 6-chloro-7-methoxy-4(1H)-quinolones efficacious against multiple stages of Plasmodium.

Authors:  R Matthew Cross; David L Flanigan; Andrii Monastyrskyi; Alexis N LaCrue; Fabián E Sáenz; Jordany R Maignan; Tina S Mutka; Karen L White; David M Shackleford; Ian Bathurst; Frank R Fronczek; Lukasz Wojtas; Wayne C Guida; Susan A Charman; Jeremy N Burrows; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2014-10-22       Impact factor: 7.446
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  5 in total

1.  Progress in the Optimization of 4(1H)-Quinolone Derivatives as Antimalarials Targeting the Erythrocytic, the Exoerythrocytic and the Transmitting Stages of the Malaria Parasite.

Authors:  Fabian Brockmeyer; Roman Manetsch
Journal:  Chimia (Aarau)       Date:  2017-04-26       Impact factor: 1.656

2.  Aminoalkoxycarbonyloxymethyl Ether Prodrugs with a pH-Triggered Release Mechanism: A Case Study Improving the Solubility, Bioavailability, and Efficacy of Antimalarial 4(1H)-Quinolones with Single Dose Cures.

Authors:  Andrii Monastyrskyi; Fabian Brockmeyer; Alexis N LaCrue; Yingzhao Zhao; Steven P Maher; Jordany R Maignan; Vivian Padin-Irizarry; Yana I Sakhno; Prakash T Parvatkar; Ami H Asakawa; Lili Huang; Debora Casandra; Sherwin Mashkouri; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2021-05-12       Impact factor: 8.039

3.  A New Scalable Synthesis of ELQ-300, ELQ-316, and other Antiparasitic Quinolones.

Authors:  Sovitj Pou; Rozalia A Dodean; Lisa Frueh; Katherine M Liebman; Rory T Gallagher; Haihong Jin; Robert T Jacobs; Aaron Nilsen; David R Stuart; J Stone Doggett; Michael K Riscoe; Rolf W Winter
Journal:  Org Process Res Dev       Date:  2021-08-04       Impact factor: 3.858

4.  Synthesis of quinolines via sequential addition and I2-mediated desulfurative cyclization.

Authors:  Mingming Yang; Yajun Jian; Weiqiang Zhang; Huaming Sun; Guofang Zhang; Yanyan Wang; Ziwei Gao
Journal:  RSC Adv       Date:  2021-12-06       Impact factor: 4.036

5.  Synthesis, biological evaluation, and molecular modelling studies of potent human neutrophil elastase (HNE) inhibitors.

Authors:  Maria Paola Giovannoni; Igor A Schepetkin; Mark T Quinn; Niccolò Cantini; Letizia Crocetti; Gabriella Guerrini; Antonella Iacovone; Paola Paoli; Patrizia Rossi; Gianluca Bartolucci; Marta Menicatti; Claudia Vergelli
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051
  5 in total

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