scholarly journals Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes

RSC Advances ◽  
2020 ◽  
Vol 10 (72) ◽  
pp. 44183-44190
Author(s):  
Jonathon P. Matheny ◽  
Pavel M. Yamanushkin ◽  
Peter A. Petillo ◽  
Michael Rubin
Keyword(s):  
Nucleophilic Addition ◽  
Functional Group ◽  
Strain Release

The sulfonamide moiety was evaluated as an activating and stabilizing functional group in the metal templated strain release-driven intramolecular nucleophilic addition of amines to cyclopropenes to generate 1,5-diazocan-2-ones.

scholarly journals Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 230 ◽  
Author(s):  
Elwira Bisz ◽  
Michal Szostak
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
High Selectivity ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Grignard Reagents ◽  
High Importance ◽  
Iron Salts ◽  
The Cross

Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

Tuning the Molecular Sensitivity of Conductive Polymer Resistive Sensors by Chemical Functionalization

2014 ◽  
Vol 605 ◽  
pp. 597-600 ◽  
Author(s):  
Evelina Frontera ◽  
Pablo C. Cavallo ◽  
Robert Olejnik ◽  
Diego F. Acevedo ◽  
Petr Slobodian ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Functional Group ◽  
Alkyl Chain ◽  
Conductive Polymer ◽  
The Other ◽  
Measuring System ◽  
Chemical Functionalization ◽  
Volatile Organic ◽  
Resistive Sensor ◽  
Long Alkyl Chain

Polyaniline thin films are chemically functionalized by nucleophilic addition of thiols beareing different functional groups: carboxylic, amine, -dodecyl and sulfonic. The modification is tested using FTIR and XPS spectroscopy. Then, the films are used as resistive sensors for different volatile organic compounds in a static measuring system. The sensitivity of conducting polymers to alcohols and heptane is strongly affected by the chemical functionalization of the materials. Polyaniline show an increasing signal when the chain length of different alcohols is increased. The incorporation of hydrophilic groups on the PANI chains seems to maintain the trend. On the other hand, the polymer modified with a long alkyl chain (PANI-DOT) show negative response for methanol and the signal increases up to propanol to decrease for longer chains. PANI-DOT show the largest signal for heptane of all polymers tested. Therefore, the functional group attached to the conductive polymer chain can be used to tune the molecular sensitivity of the resistive sensor

scholarly journals Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 463
Author(s):  
Julin Gong ◽  
Kun Hu ◽  
Yetong Zhang ◽  
Yinlin Shao ◽  
Tianxing Cheng ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
Synthetic Pathway ◽  
Arylboronic Acids ◽  
Palladium Catalyzed ◽  
Plausible Mechanism

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moderate to good yields. A plausible mechanism for the formation of 2,4-diarylquinazolines involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed.

Transition-metal-free synthesis of 5-amino-1,2,3-triazoles via nucleophilic addition/cyclization of carbodiimides with diazo compounds

2021 ◽  
Author(s):  
Shilong Wang ◽  
Yuanyuan Zhang ◽  
Guixin Liu ◽  
Hui Xu ◽  
Lijuan Song ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
Diazo Compounds ◽  
Metal Free

A facile and transition-metal-free synthesis of functionalized 5-amino-1,2,3-triazoles with good functional-group tolerance and regioselectivity via nucleophilic addition/cyclization has been described.

scholarly journals Me3Al mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; A convenient approach for the synthesis of substituted 1-aminoisoquinolines

2021 ◽  
Author(s):  
Midhun Sai Krishna Adusumalli ◽  
Lakshmi Narayana Sharma Konidena ◽  
Hima Bindu Gandham ◽  
Krishnaiah Kumari ◽  
Krishna Reddy Valluru ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Functional Group ◽  
Antitumor Agent ◽  
Synthetic Utility ◽  
Convenient Approach ◽  
Reaction Proceeds ◽  
Substituted 1

A simple and efficient protocol for the construction of 1-aminoisoquinolines was achieved by treating 2-(2-oxo-2-phenylethyl)benzonitriles with amines in the presence of Me3Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramolecular cyclisation. This method provides wide variety of substituted 1-aminoisoquinolines with good functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of antitumor agent CWJ-a-5 in gram scale.

scholarly journals Me3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

2021 ◽  
Vol 17 ◽  
pp. 2765-2772
Author(s):  
Krishna M S Adusumalli ◽  
Lakshmi N S Konidena ◽  
Hima B Gandham ◽  
Krishnaiah Kumari ◽  
Krishna R Valluru ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Functional Group ◽  
Antitumor Agent ◽  
Synthetic Utility ◽  
Convenient Approach ◽  
Reaction Proceeds ◽  
Substituted 1

A simple and efficient protocol for the construction of 1-aminoisoquinolines was achieved by treating 2-(2-oxo-2-phenylethyl)benzonitriles with amines in the presence of Me3Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramolecular cyclisation. This method provides a wide variety of substituted 1-aminoisoquinolines with good functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5 in gram scale.

Acetic Anhydride Mediated Retro-Ene Reaction via a [4.4.3]Propel­lane Skeleton Intermediate Containing a Quaternary Ammonium Linkage

Synthesis ◽  
2017 ◽  
Vol 50 (21) ◽  
pp. 4263-4269 ◽  
Author(s):  
Hiroshi Nagase ◽  
Noriki Kutsumura ◽  
Takahiro Okada ◽  
Satomi Imaide ◽  
Hideaki Fujii
Keyword(s):  
Reaction Mechanism ◽  
Acetic Anhydride ◽  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
Acetoxy Group ◽  
Ene Reaction ◽  
Deuterated Derivative ◽  
Nitrogen Functional Group

A novel retro-ene reaction via a [4.4.3]propellane intermediate containing a quaternary ammonium linkage was developed. The feature of this acetic anhydride mediated rearrangement includes the elimination of an acetoxy group at the C14 position and subsequent intramolecular nucleophilic addition of a nitrogen functional group to form an isolable ammonium salt intermediate. We clarified the reaction mechanism utilizing the deuterated derivative.

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