Tandem Nucleophilic Addition/Cyclization Reaction in the Synthesis of Ketimine-Type Iminosugars

2008 ◽  
Vol 73 (9) ◽  
pp. 3612-3615 ◽  
Author(s):  
Jean-Bernard Behr ◽  
Adel Kalla ◽  
Dominique Harakat ◽  
Richard Plantier-Royon
Keyword(s):  
Nucleophilic Addition ◽  
Cyclization Reaction

scholarly journals Cobalt-Catalyzed Cyclization of 2-Bromobenzamides with Carbodiimides: A New Route for the Synthesis of 3-(Imino)isoindolin-1-ones

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7212
Author(s):  
Hasil Aman ◽  
Yu-Chiao Huang ◽  
Yu-Hao Liu ◽  
Yu-Lin Tsai ◽  
Min Kim ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Catalytic Reaction ◽  
Nucleophilic Addition ◽  
Cyclization Reaction ◽  
Synthetic Pathway

A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.

scholarly journals Copper (triazole-5-yl)methanamine complexes onto MCM-41: the synthesis of pyridine-containing pseudopeptides through the 6-endo-dig cyclization of 1,5-enynes

RSC Advances ◽  
2020 ◽  
Vol 10 (18) ◽  
pp. 10577-10583
Author(s):  
Neda Akbarikalani ◽  
Kamran Amiri ◽  
Ahmed Al-Harrasi ◽  
Saeed Balalaie
Keyword(s):  
Nucleophilic Addition ◽  
Cyclization Reaction ◽  
Enyne Cyclization ◽  
Mcm 41

A sequential Ugi/nucleophilic addition/1,5-enyne cyclization reaction was used for the synthesis of pseudopeptides containing pyridine skeletons in the presence of Cu@TZMA@MCM-41.

One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 857-859 ◽  
Author(s):  
Fen Tan ◽  
Zheng-Zheng Meng ◽  
Xiao-Qin Xiong ◽  
Guo-Ping Zeng ◽  
Ming-Wu Ding
Keyword(s):  
Nucleophilic Addition ◽  
Cyclization Reaction ◽  
Regioselective Synthesis ◽  
One Pot ◽  
Tosyl Chloride ◽  
Aryl Isocyanates ◽  
Wittig Reactions

A new, one-pot, regioselective preparation of 2,5,6,7-tetrahydroimidazo[1,2-a]imidazol-3-ones by a sequential aza-Wittig/nucleophilic addition/cyclization reaction was developed. The aza-Wittig reactions of ethyl (2Z)-3-aryl-2-[(triphenylphosphoranylidene)amino] acrylates with aryl isocyanates produced carbodiimide intermediates that were then treated sequentially with 2-aminoethanol and tosyl chloride/triethylamine to give the corresponding (2Z)-2-[(substituted)benzylidene]-2,5,6,7-tetrahydro-3H-imidazo[1,2-a]imidazol-3-ones in good overall yields and with high regioselectivity.

One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2402-2408
Author(s):  
Zhi-Rong Guan ◽  
Shuai Liu ◽  
Zi-Ming Liu ◽  
Ming-Wu Ding
Keyword(s):  
Nucleophilic Addition ◽  
Wittig Reaction ◽  
Cyclization Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Sodium Alkoxide

A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

Synthesis of Novel Bis-pyrazoles via Electrophilic Cyclization

2019 ◽  
Vol 16 (6) ◽  
pp. 511-516
Author(s):  
Adnan Cetin
Keyword(s):  
13C Nmr ◽  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Pyrazole Derivatives ◽  
Spectral Analyses ◽  
Mass Spectral ◽  
Palladium Catalyzed ◽  
Ft Ir ◽  
Reaction Compound

Efficient steps towards the synthesis of novel (phenyl)(1'-aryl-1,5,5'-triphenyl[3,3'-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of α,β-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

1989 ◽  
Vol 54 (2) ◽  
pp. 440-445 ◽  
Author(s):  
Vladimír Macháček ◽  
Alexandr Čegan ◽  
Miloš Sedlák ◽  
Vojeslav Štěrba
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Equilibrium Constant ◽  
Mole Fraction ◽  
Nucleophilic Addition ◽  
Adduct Formation ◽  
First Case ◽  
C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

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