Synthesis and NMR Studies of Activated Derivatives ofcis- andtrans-5-Amino-6-oxopiperidine-2-carboxylic Acid and the Corresponding Bicyclic Dilactam 2,5-DBO: Potential Building Blocks for Stereoregular Polyamides and Peptides

1999 ◽  
Vol 32 (20) ◽  
pp. 6507-6516 ◽  
Author(s):  
F. A. Al-Obeidi ◽  
B. J. M. Micheli ◽  
M. Barfield ◽  
A. B. Padias ◽  
Y. Wei ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Nmr Studies

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

2019 ◽  
Author(s):  
Ming Shang ◽  
Karla S. Feu ◽  
Julien C. Vantourout ◽  
Lisa M. Barton ◽  
Heather L. Osswald ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Carbon Centers ◽  
Drug Candidates ◽  
Rapid Diversification ◽  
Directing Group ◽  
Compound Series

<div> <div> <div> <p>The union of two powerful transformations, directed C–H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series. </p> </div> </div> </div>

Design, synthesis and evaluation of structurally diverse ortho-acylphenol-diindolylmethane hybrids as anticancer agents

2022 ◽  
Author(s):  
Zhi-Gang Yin ◽  
Xiong-Wei Liu ◽  
Hui-Juan Wang ◽  
Min Zhang ◽  
Xiong-Li Liu ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Anticancer Agents ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Design Synthesis ◽  
Pyrone Ring ◽  
Ring Opening Reaction ◽  
First Time

A highly efficient synthesis of structurally diverse ortho-acylphenol–diindolylmethane hybrids 3 using carboxylic acid-activated chromones as versatile synthetic building blocks is reported here for the first time, through 1,4-nucleophilic addition and followed by a decarboxylation and pyrone ring opening reaction process.

scholarly journals Harnessing Chemical Energy for the Activation and Joining of Prebiotic Building Blocks

2019 ◽  
Author(s):  
Ziwei Liu ◽  
Long-Fei Wu ◽  
Jianfeng Xu ◽  
Claudia Bonfio ◽  
David Russell ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Carboxylic Acid ◽  
Peptide Nucleic Acid ◽  
Reactive Intermediates ◽  
Building Blocks ◽  
Acid System ◽  
Rna Oligomers ◽  
Prebiotic Activation ◽  
Simultaneous Activation ◽  
Acid Anhydrides

Simultaneous activation of carboxylates and phosphates provides multiple pathways for the generation of reactive intermediates, including mixed carboxylic acid-phosphoric acid anhydrides, for the synthesis of peptidyl-RNAs, peptides, RNA oligomers and primordial phospholipids. These results indicate that unified prebiotic activation chemistry could have enabled the joining of building blocks in aqueous solution from a common pool and enabled the progression of a system towards higher complexity foreshadowing the modern encapsulated peptide-nucleic acid system

ChemInform Abstract: NMR Studies of Four Isomers of Decahydroisoquinoline-3(S)-carboxylic Acid (I) and a Potent HIV Proteinase Inhibitor Incorporating the (S,S, S) Isomer.

ChemInform ◽  
2010 ◽  
Vol 24 (22) ◽  
pp. no-no
Author(s):  
J. C. GILBERT ◽  
S. REDSHAW ◽  
H. S. SIMMONITE ◽  
W. A. THOMAS ◽  
I. W. A. WHITCOMBE
Keyword(s):  
Carboxylic Acid ◽  
Proteinase Inhibitor ◽  
Nmr Studies

Use of 3-(Pentafluorosulfanyl)phenol to Access to Advanced Substituted Pentafluorosulfanylphenol/anisole: Application to the Synthesis of 2-(Arylpentafluorosulfanyl)indanedione

2021 ◽  
Vol 18 ◽  
Author(s):  
Antoine Michaut ◽  
Sabrina Quatrevaux ◽  
Laurence Queguiner ◽  
Sandrine Gaurrand ◽  
Jérôme Guillemont
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
The Future

Abstract: The synthesis of advanced substituted 3-pentafluorosulfanylphenol/anisole was accomplished starting from the easy to access and commercially available 3-pentafluorosulfanylphenol. These products bear diverse substitutions such as ester, aldehyde, halogens, alcohol, nitrile and carboxylic acid and could be in the future used as high value building blocks for the synthesis of various scaffolds. For our part, this intermediate had been used to synthetize a library of 2-arylindadiones substituted by a pentafluorosulfanyl group.

scholarly journals Modular triazine-based carborane-containing carboxylic acids – synthesis and characterisation of potential boron neutron capture therapy agents made of readily accessible building blocks

2019 ◽  
Vol 48 (29) ◽  
pp. 10834-10844 ◽  
Author(s):  
Martin Kellert ◽  
Dennis J. Worm ◽  
Paul Hoppenz ◽  
Menyhárt B. Sárosi ◽  
Peter Lönnecke ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Building Blocks ◽  
Neutron Capture Therapy ◽  
Boron Neutron Capture

Boron-rich carboxylic acid derivatives were synthesised as coupling partners for tumour-selective biomolecules with applications as selective BNCT agents.

Multigram Synthesis of C4/C5 3,3-Difluorocyclobutyl-Substituted Building Blocks

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4949-4957 ◽  
Author(s):  
Sergey Ryabukhin ◽  
Kostiantyn Melnykov ◽  
Dmitriy Granat ◽  
Dmitriy Volochnyuk ◽  
Oleksandr Grygorenko
Keyword(s):  
Carboxylic Acid ◽  
Alternative Pathway ◽  
Building Blocks ◽  
Tert Butyl ◽  
Synthetic Intermediate

An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (including carboxylic acid, amines, alcohols, azide, trifluoroborate ketone) is described. It is shown that, in most cases, ethyl 3,3-difluorocyclobutanecarboxylate is a convenient common synthetic intermediate to obtain the target derivatives. For preparation of 3,3-difluorocyclobutanol or -cyclobutanone, an alternative pathway via reaction of dichloroketene and tert-butyl or benzyl vinyl­ ether should be applied.

Synthesis of all-aliphatic polyamide dendrimers based on a 3,3′-diaminopivalic acid scaffold

2015 ◽  
Vol 6 (16) ◽  
pp. 3031-3038 ◽  
Author(s):  
Antonio Jesus Ruiz-Sanchez ◽  
Pablo Mesa-Antunez ◽  
Nekane Barbero ◽  
Daniel Collado ◽  
Yolanda Vida ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Aliphatic Polyamide

Iterative 3,3′-diaminopivalic acid connections act as building blocks in the production of new all-aliphatic polyamide dendrimers. 3,3′-Diazidopivalic acid units underpin a two-step pathway involving carboxylic acid–amine condensation, followed azide reduction.

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