ChemInform Abstract: Regioselective Ring-Opening Nucleophilic Addition of Aziridines Through Photoredox Catalyst.

ChemInform ◽  
2015 ◽  
Vol 46 (11) ◽  
pp. no-no
Author(s):  
Hongnan Sun ◽  
Chao Yang ◽  
Run Lin ◽  
Wujiong Xia
Keyword(s):  
Nucleophilic Addition ◽  
Ring Opening

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.

Nitric acid promoted formation of an N-confused porphyrin-derived porphodimethene and a violinoid

2006 ◽  
Vol 10 (07) ◽  
pp. 953-961 ◽  
Author(s):  
Chen-Hsiung Hung ◽  
Chia-Chi Liaw ◽  
Wei-Ming Chin ◽  
Gao-Fong Chang ◽  
Chuan-Hung Chuang
Keyword(s):  
Crystal Structure ◽  
Nitro Group ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Pyrrole Ring ◽  
Hydroxyl Group ◽  
Parallel Reaction ◽  
Free Base ◽  
Hydrogen Bonding Interactions ◽  
Open Ring

The nitration of free-base N -confused porphyrin led to a novel 5,10-meso-dihydroxy- N -confused porphodimethene and an open-ring N -confused violinoid. The results support nitration occurring first, followed by nucleophilic addition of a hydroxyl group and a parallel reaction of oxygenolysis to cause the ring-opening. The nitro group substituted at the inner carbon of the inverted pyrrole ring is located on both the porphodimethene and violinoid. In the case of the porphodimethene, two dihydroxyl groups with υ( OH ) at 3404 cm−1 are arranged in a syn conformation at the same side with the nitro group. The violinoid exhibits υ( C = O ) at 1659 cm−1. NMR and structure determination suggest that oxygenolysis occurs selectively at the C=C bond between the α-pyrrole and meso carbon closest to the amino NH of the inverted pyrrole ring. The single crystal structure of porphodimethene gave a 50% disorder between the peripheral nitrogen and carbon atom on the inverted pyrrole ring, while a dimeric structure assembled through hydrogen bonding interactions was observed in the crystal lattice of the violinoid.

Nucleophilic addition of amines, alcohols, and thiophenol with epoxide/olefin using highly efficient zirconium metal organic framework heterogeneous catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (36) ◽  
pp. 28270-28280 ◽  
Author(s):  
Poonam Rani ◽  
Rajendra Srivastava
Keyword(s):  
Heterogeneous Catalyst ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Metal Organic Framework ◽  
Wide Range ◽  
Excellent Activity ◽  
Metal Organic ◽  
Ring Opening Of Epoxides ◽  
Activated Olefins ◽  
Zirconium Metal

Zr based MOF exhibited excellent activity in the ring opening of epoxides/nucleophilic addition of activated olefins with wide range of nucleophiles.

ChemInform Abstract: Oxovanadium(V)-Induced Tandem Nucleophilic Addition and Oxidative Ring-Opening Transformation.

ChemInform ◽  
2010 ◽  
Vol 26 (8) ◽  
pp. no-no
Author(s):  
T. HIRAO ◽  
T. FUJII ◽  
T. TANAKA ◽  
Y. OHSHIRO
Keyword(s):  
Nucleophilic Addition ◽  
Ring Opening

scholarly journals Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3700
Author(s):  
Yu Zhao ◽  
Zitong Zhou ◽  
Man Chen ◽  
Weiguang Yang
Keyword(s):  
Nucleophilic Addition ◽  
Ring Opening ◽  
Room Temperature ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Sulfonyl Azides ◽  
The Stability

N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

Theoretical investigation of the mechanism of DMAP-promoted [4 + 2]-annulation of prop-2-ynylsulfonium with isatoic anhydride

2022 ◽  
pp. 1-9
Author(s):  
Nan Lu ◽  
Hui Liang ◽  
Chengxia Miao ◽  
Xiaozheng Lan ◽  
Ping Qian
Keyword(s):  
Nucleophilic Addition ◽  
Ring Opening ◽  
Bond Order ◽  
Frontier Molecular Orbital ◽  
Methyl Groups ◽  
Isatoic Anhydride ◽  
Intramolecular Cycloaddition ◽  
Double Bond Isomerization ◽  
Stage 1 ◽  
Mayer Bond Order

The mechanism for DMAP-promoted [4 + 2]-annulation of prop-2-ynylsulfonium with isatoic anhydride is investigated using the M06-2X functional. The reaction comprises isomerization of prop-2-ynylsulfonium in stage 1. Stage 2 includes DMAP-promoted deprotonation, nucleophilic addition, ring opening, and decarboxylation. Three steps of intramolecular cycloaddition, DMAP-promoted protonation, and dealkylation occur in stage 3, generating methylated DMAP and neutral thioether, which undergo double-bond isomerization to yield 3-methylthio-4-quinolone. The ability of DMAP to promote the reaction lies in the barrier decrease for alkyne isomerization, deprotonation/protonation of allenes, and dealkylation as effective bases for transferring protons and methyl groups. The roles of prop-2-ynylsulfonium and isatoic anhydride were demonstrated to be C2 and C4 synthons via Multiwfn analysis on the frontier molecular orbital. An alternative path was also confirmed by the Mayer bond order of the vital transition states.

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