Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

2020 ◽  
Vol 7 (3) ◽  
pp. 525-530 ◽  
Author(s):  
Ilia A. Smetanin ◽  
Anastasiya V. Agafonova ◽  
Nikolai V. Rostovskii ◽  
Alexander F. Khlebnikov ◽  
Dmitry S. Yufit ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Diazo Compounds ◽  
Convergent Assembly

A highly convergent assembly of 3,4-epoxypyrroline derivatives from azirines, diazo compounds and amines is developed based on the domino cyclization of 6-halo-1-oxa-4-azahexatrienes.

scholarly journals DFT investigation on mechanism of dirhodium tetracarboxylate-catalyzed O-H insertion of diazo compounds with H2O

2010 ◽  
Vol 8 (1) ◽  
pp. 223-228 ◽  
Author(s):  
Zhenfeng Liu ◽  
Jianyong Liu
Keyword(s):  
Dft Calculations ◽  
Nucleophilic Addition ◽  
Diazo Compound ◽  
Experimental Results ◽  
Diazo Compounds ◽  
Reaction Pathways ◽  
Insertion Reaction ◽  
Oxonium Ylides ◽  
Oxonium Ylide ◽  
Very High

AbstractThe mechanism of the dirhodium tetracarboxylate-catalyzed O-H insertion reaction of diazomethane and methyl diazoacetate with H2O has been studied in detail using DFT calculations. The rhodium catalyst and a diazo compound couple to form a rhodiumcarbene complex. Of two reaction pathways of the Rh(II)-carbene complex with H2O, the stepwise pathway is more preferable than the concerted one. Formation of a Rh(II) complex-associated oxonium ylide is an exothermal process, and direct decomposition of the ylide gives a very high barrier. The high barriers for the 1,2-H shift of Rh(II) complex-associated oxonium ylides make the ylides become stable intermediates in both reactions, especially for the reactions in solution. Difficulty in formation of a free oxonium ylide supports experimental results, indicating that the Rh(II) complex-catalyzed nucleophilic addition of a diazo compound proceeds via a Rh(II) complex-associated oxonium ylide rather than via a free oxonium ylide.

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.

A Rh(II)- or Ag(I)-Catalyzed Formal C–O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate

Synlett ◽  
2021 ◽  
Author(s):  
Wenhao Hu ◽  
Cong Xu ◽  
Xiangrong Liu ◽  
Xiongda Xie ◽  
Lin Deng ◽  
...  
Keyword(s):  
Reactive Intermediates ◽  
Diazo Compounds ◽  
Synthetic Method ◽  
Amino Ester ◽  
Tertiary Carbon ◽  
Convergent Assembly

AbstractA mild and facile synthetic method via convergent assembly of two reactive intermediates generated in situ has been developed. This method provides an efficient way to construct six- and seven-membered N-heterocycles containing a biaryl linkage. This reaction features a gem-difunctionalization process of diazo compounds with cyclic hemiaminals, delivering α-hydroxyl-β-amino ester derivatives with a tertiary carbon center through a formal C–O bond-insertion transformation.

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.

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.

New catalysts for the reduction of aromatic diazo compounds by alcohols to hydrocarbons

1983 ◽  
Vol 32 (4) ◽  
pp. 858-861 ◽  
Author(s):  
V. S. Lenenko ◽  
A. P. Borisov ◽  
V. D. Makhaev ◽  
E. I. Mysov ◽  
V. B. Shur ◽  
...  
Keyword(s):  
Diazo Compounds
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