ChemInform Abstract: NUCLEOPHILIC SUBSTITUTION AT THE ATOM OF TWO-COORDINATE PHOSPHORUS. NEW SYNTHETIC APPROACH TO METHYLENEPHOSPHINES WITH THIOALKYL SUBSTITUENTS

1984 ◽  
Vol 15 (44) ◽  
Author(s):  
V. D. ROMANENKO ◽  
L. K. POLYACHENKO ◽  
L. N. MARKOVSKII
Keyword(s):  
Nucleophilic Substitution ◽  
Synthetic Approach

scholarly journals The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

2015 ◽  
Vol 11 ◽  
pp. 385-391 ◽  
Author(s):  
Marina V Goryaeva ◽  
Yanina V Burgart ◽  
Marina A Ezhikova ◽  
Mikhail I Kodess ◽  
Viktor I Saloutin
Keyword(s):  
Nucleophilic Substitution ◽  
Alternative Pathway ◽  
Synthetic Approach ◽  
Reaction Routes

The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

Modification of β-positions in porphyrazines by substitution reactions

2000 ◽  
Vol 04 (05) ◽  
pp. 555-563 ◽  
Author(s):  
OL'GA G. KHELEVINA ◽  
NATALIYA V. CHIZHOVAN ◽  
PAVEL A. STUZHIN
Keyword(s):  
Nucleophilic Substitution ◽  
Synthetic Approach ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Radical Substitution

Peripheral modification of the porphyrazine macrocycle is an important synthetic approach to β-substituted porphyrazine derivatives, especially those which cannot be obtained via direct template cyclotetramerization of maleodinitriles and other similar synthons. The paper presents the last results of the systematical investigation of the reactivity of unsubstituted porphyrazine (tetraazaporphine) in the reactions of electrophilic and radical substitution in pyrrole rings (bromination, chlorination, chloromethylation, nitration and sulfonation) and nucleophilic substitution reactions of chloro-, bromo- and sulfo-substituted porphyrazines.

scholarly journals Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

2020 ◽  
Vol 16 ◽  
pp. 2880-2887
Author(s):  
Danny Lainé ◽  
Vincent Denavit ◽  
Olivier Lessard ◽  
Laurie Carrier ◽  
Charles-Émile Fecteau ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Fluorine Atom ◽  
Synthetic Approach ◽  
Nucleophilic Fluorination

In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1HF. The influence of the fluorine atom at C2 on reactivity at C4 could contribute to a new fluorine effect in nucleophilic substitution. Finally, with the continuous objective of synthesizing novel multi-vicinal fluorosugars, we prepared one difluorinated and one trifluorinated alditol analogue.

Modular synthesis of carbazole substituted phthalimides as potential photocatalysts

Synthesis ◽  
2021 ◽  
Author(s):  
Zsombor Gonda ◽  
Tamás Földesi ◽  
Bálint Nagy ◽  
Zoltán Novák
Keyword(s):  
Metal Complexes ◽  
Nucleophilic Substitution ◽  
Noble Metal ◽  
High Variability ◽  
Synthetic Approach ◽  
Aromatic Nucleophilic Substitution ◽  
Modular Synthesis ◽  
Comparable Activity ◽  
Acid Anhydrides

Herein, we report the modular synthesis of carbazole functionalized phthalimides (PI), and demonstrated their applicability as catalyst in selected photocatalytic transformations. The developed synthetic approach provides high variability of phthalimide considering that the synthesis of the phthalimide core can be easily performed. Starting from fluorophthalic acid anhydrides, the corresponding fluorophthalimides were prepared with various amines, and the fluoro function ensured the introduction of carbazoles into the phthalimide framework through aromatic nucleophilic substitution. Besides the synthetic developments, we tested some of the carbazolyl phthalimides in four different photocatalytic transformations, and found attractive and comparable activity to the known 4-CzIPN and noble metal complexes.

scholarly journals (E)-3-(Aryl(arylamino)Methylene)Indolin-2-One Derivatives: An Efficient Synthetic Approach and Evaluation of their Cancer Inhibitory Activity

2018 ◽  
Vol 42 (1) ◽  
pp. 44-49 ◽  
Author(s):  
Hongwu Jiang ◽  
Zhiyuan Feng ◽  
Taiping Chen ◽  
Zicheng Li ◽  
Wencai Huang ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Nucleophilic Substitution ◽  
Cell Lines ◽  
Inhibitory Activity ◽  
Synthetic Approach ◽  
Substituted Anilines ◽  
Hct 116 ◽  
Aryl Methyl ◽  
Simultaneous Elimination

A series of (E)-3-(aryl(arylamino)methylene)indolin-2-one derivatives were synthesised using an efficient synthetic approach. The method involved reaction of 3-bromo-3-(bromo(aryl)methyl)indolin-2-one with substituted anilines through nucleophilic substitution and a simultaneous elimination using NaHCO3 in DMF. The anticancer activity of the products against four cell lines, HCT-116, A549, SKOV3 and MDA-MB-231, was also evaluated, and several compounds showed moderate inhibitory activity.

scholarly journals Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

2018 ◽  
Vol 14 ◽  
pp. 2618-2626 ◽  
Author(s):  
Lidia A Smyshliaeva ◽  
Mikhail V Varaksin ◽  
Pavel A Slepukhin ◽  
Oleg N Chupakhin ◽  
Valery N Charushin
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Advanced Materials ◽  
Synthetic Approach ◽  
Nucleophilic Substitution Of Hydrogen ◽  
One Pot ◽  
Metal Free

The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (SN H) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials.

New Insights into the Nature of the Band Gap of CuGeO3 Nanoparticles: Synthesis, Electronic Structure, and Optical and Photocatalytic Properties

2019 ◽  
Author(s):  
Victor Y. Suzuki ◽  
Luís Henrique Cardozo Amorin ◽  
Natália H. de Paula ◽  
Anderson R. Albuquerque ◽  
Julio Ricardo Sambrano ◽  
...  
Keyword(s):  
Electronic Structure ◽  
Band Gap ◽  
Material Design ◽  
Photocatalytic Properties ◽  
Critical Parameters ◽  
Synthetic Approach ◽  
Microwave Assisted ◽  
Theoretical Approaches ◽  
Nanoparticles Synthesis ◽  
First Time

<p>We report, for the first time, new insights into the nature of the band gap of <a>CuGeO<sub>3</sub> </a>(CGO) nanocrystals synthesized from a microwave-assisted hydrothermal method in the presence of citrate. To the best of our knowledge, this synthetic approach has the shortest reaction time and it works at the lowest temperatures reported in the literature for the preparation of these materials. The influence of the surfactant on the structural, electronic, optical, and photocatalytic properties of CGO nanocrystals is discussed by a combination of experimental and theoretical approaches, and that results elucidates the nature of the band gap of synthetized CGO nanocrystals. We believe that this particular strategy is one of the most critical parameters for the development of innovative applications and that result could shed some light on the emerging material design with entirely new properties.</p> <p><b> </b></p>

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

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