The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1,3-dipolar cycloadditions of azides and alkynes

Mohtat, Bita; Siadati, Seyyed Amir; Khalilzadeh, Mohammad A.; Zareyee, Daryoush

doi:10.1016/j.molstruc.2017.10.034

Cited by 16 publications

(11 citation statements)

References 49 publications

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“…This method, as we have proven, it's the most powerful instrument for studying and understanding the molecular mechanism of various types of reactions. [30][31][32][33][34][35][36][37] 2 | COMPUTATIONAL METHODS…”

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confidence: 99%

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Kącka‐Zych

2020

Int J of Quantum Chemistry

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The [4 + 1] cycloaddition (41CA) and [2 + 1] cycloaddition (21CA) reactions of the α-halogeno-nitroalkenes with carbene have been studied using the molecular electron density theory through density functional theory calculations at the MPWB1K(PCM)/ 6-311G(d,p) computational level. The 41CA reaction take place through a polar twostep mechanism involving the formation of a zwitterionic intermediate. The competitive 21CA reaction path proceeds according to nonconcerted two-stage one-step. Bonding evolution theory analysis of 41CA reaction allows the distinguishing of four groups along the reaction path. The reaction begins with rupture of the C C double bond of the alkene moiety and formation of the pseudoradical center. Formation of the O C and C C new single bonds begins in subsequent phases. In the last stage of the 41CA reaction path, we observed the formation of an N C new double bond. In the case of 21CA reaction path, we observed the successive rupture of the C C double bond of the alkene moiety, formation of C C new single bond and pseudoradical center, and creation of a second C C single bond.

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confidence: 99%

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Kącka‐Zych

2020

Int J of Quantum Chemistry

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“…Nitrogen-based heterocyclic systems are commonly found in pharmaceutical agents and natural products, and they have been intensively explored as new bioactive products [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. Among them, the indazoles [ 11 , 12 , 13 , 14 , 15 , 16 ] are favored by synthetic and medicinal chemists, as evidenced by their widespread abundance in pharmaceuticals and natural products.…”

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confidence: 99%

Recent Strategies in Transition-Metal-Catalyzed Sequential C–H Activation/Annulation for One-Step Construction of Functionalized Indazole Derivatives

et al. 2022

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Designing new synthetic strategies for indazoles is a prominent topic in contemporary research. The transition-metal-catalyzed C–H activation/annulation sequence has arisen as a favorable tool to construct functionalized indazole derivatives with improved tolerance in medicinal applications, functional flexibility, and structural complexity. In the current review article, we aim to outline and summarize the most common synthetic protocols to use in the synthesis of target indazoles via a transition-metal-catalyzed C–H activation/annulation sequence for the one-step synthesis of functionalized indazole derivatives. We categorized the text according to the metal salts used in the reactions. Some metal salts were used as catalysts, and others may have been used as oxidants and/or for the activation of precatalysts. The roles of some metal salts in the corresponding reaction mechanisms have not been identified. It can be expected that the current synopsis will provide accessible practical guidance to colleagues interested in the subject.

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“…21–24 Also, Born–Oppenheimer molecular dynamics (BOMD) simulations were applied to identify any possible species which could emerge during the reaction. 25,26…”

Section: Introductionmentioning

confidence: 99%

“…[21][22][23][24] Also, Born-Oppenheimer molecular dynamics (BOMD) simulations were applied to identify any possible species which could emerge during the reaction. 25,26 Computational A number of hypothetical geometries containing different orientations were developed as input files for each predicted species and were then optimized to give any reliable states. This resulted in finding a number of stable and metastable states for the reactants, products, and transition states (TSs).…”

Section: Introductionmentioning

confidence: 99%

A [1 + 2] cycloaddition instead of usual [2 + 3] cycloaddition between the B₁₂N₁₂ cluster and methyl azide: Potential energy surface calculations and Born–Oppenheimer molecular dynamics simulations

Pakravan

Siadati

2020

Progress in Reaction Kinetics and Mechanism

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We have examined here the possibility of functionalization of the B12N12 cluster by methyl azide by means of a [2 + 3] cycloaddition reaction in analogy with the spontaneous functionalization of C20 fullerene using the same reaction. To achieve more reliable data, all possible interactions at different positions and orientations were considered by reaction channel study and potential energy surface calculations. Also, Born–Oppenheimer molecular dynamics simulations were used to find probable species which could emerge during the reactions.

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The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1,3-dipolar cycloadditions of azides and alkynes

Cited by 16 publications

References 49 publications

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Recent Strategies in Transition-Metal-Catalyzed Sequential C–H Activation/Annulation for One-Step Construction of Functionalized Indazole Derivatives

A [1 + 2] cycloaddition instead of usual [2 + 3] cycloaddition between the B₁₂N₁₂ cluster and methyl azide: Potential energy surface calculations and Born–Oppenheimer molecular dynamics simulations

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The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1,3-dipolar cycloadditions of azides and alkynes

Cited by 16 publications

References 49 publications

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Understanding the uniqueness of the stepwise [4 + 1] cycloaddition reaction between conjugated nitroalkenes and electrophilic carbene systems with a molecular electron density theory perspective

Recent Strategies in Transition-Metal-Catalyzed Sequential C–H Activation/Annulation for One-Step Construction of Functionalized Indazole Derivatives

A [1 + 2] cycloaddition instead of usual [2 + 3] cycloaddition between the B12N12 cluster and methyl azide: Potential energy surface calculations and Born–Oppenheimer molecular dynamics simulations

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A [1 + 2] cycloaddition instead of usual [2 + 3] cycloaddition between the B₁₂N₁₂ cluster and methyl azide: Potential energy surface calculations and Born–Oppenheimer molecular dynamics simulations