[2+2] Cycloaddition Reactions of Enamines With Electron-Deficient Acetylenes

Tunoglu, Nazan; Uludag, Nesimi

doi:10.1080/00304949709355230

Cited by 16 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The weak olefinic absorption due to the characteristic vinylic proton was observed at d = 7.00 in the spectra of the polymers 19 -39. This peak, however, was very significant and sharp (a doublet-doublet) in the spectra of the corresponding monomers 1) . The bridgehead proton of 4 also appeared in the spectrum of the polymer 49 as a triplet at d The actual average molecular masses were not determined due to the lack of standards based on the same experimental polymers.…”

Section: Resultsmentioning

confidence: 93%

See 1 more Smart Citation

Polycondensation studies of some cycloaddition products bearing carboxylate groups with ethylene glycol

Şenöz

Tunoglu²

1999

Macromol. Rapid Commun.

View full text Add to dashboard Cite

SUMMARY: Three cyclic dienamines (1 -3) and one cyclobutene adduct (4), all bearing carboxylate sidechains, were successfully reacted with ethylene glycol to synthesize new polymers. According to HPLC measurements and the results of the solubility experiments, 4 was completely converted to well soluble oligomers, whereas polyesters 19 -39 are composed of a large amount of highly insoluble structures besides some soluble oligomers. The polyesters show the characteristic bands of the corresponding monomers in the IR spectra. The NMR data gave similar results. The polyesters are rather stable and resist to oxidation.

show abstract

Section: Resultsmentioning

confidence: 93%

“…During the course of our investigation on the [2 + 2] cycloaddition reactions of enamines derived from cyclic ketones with diethyl acetylenedicarboxylate, we have synthesized cyclic dienamines 1) . In some cases, the intermediate cyclobutene adducts could be isolated.…”

Section: Introductionmentioning

confidence: 99%

Polycondensation studies of some cycloaddition products bearing carboxylate groups with ethylene glycol

Şenöz

Tunoglu²

1999

Macromol. Rapid Commun.

View full text Add to dashboard Cite

show abstract

“…Since pyrrole derivatives are building blocks for many structures including medicinal drugs, the development of a new proposed method will also contribute to the literature. Our previous studies achieved the desired target by applying DDQ and DEAD‐type compounds in different syntheses in different areas [43,44] . In this work, the relative reactivity of substituted oxime conversions is investigated, and the electron‐drawing and electron‐donating effects also involve such transformation.…”

Section: Resultsmentioning

confidence: 99%

“…Our previous studies achieved the desired target by applying DDQ and DEAD-type compounds in different syntheses in different areas. [43,44] In this work, the relative reactivity of substituted oxime conversions is investigated, and the electrondrawing and electron-donating effects also involve such transformation. As known, the substituent groups attached to the aryl ring are effective in the reaction.…”

Section: Synthesis Structure and Spectroscopic Characterizationmentioning

confidence: 99%

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Serdaroğlu,

Uludağ,

Üstün

2024

ChemistrySelect

View full text Add to dashboard Cite

The construction of pyrroles is an important heterocyclic group comprising many compounds with interesting properties that have led to numerous applications in various fields. We delineate a new synthetic method for the rapid construction of tree‐substituted pyrroles from readily available ketoximes as starting materials and also a new mechanism and method has been proposed. It is presented that substituted pyrroles were efficiently synthesized in high yields (up to 81 % yield) through the cyclization reaction of starting ketoximes mediated by 2,3‐dichlor‐5,6‐dicyanobenzoquinone (DDQ). Utilizing this protocol various pyrrole derivatives were synthesized from diethyl acetylene dicarboxylate (DEAD). We then developed the dehydrogenation reaction mechanism of this formation, also studied in detail, also all synthesized compounds were analyzed in detail by spectroscopic techniques (FT‐IR, 1H NMR, 13CNMR) which were compared with the computational data estimated at B3LYP/6‐311G** level. The thermochemical and electronic properties of the pyrroles were evaluated after optimizing and then confirming the equilibrium structures. ADMT scores were also considered to estimate/elucidate the possible bioavailability tendencies as well as the toxicity. In addition, the interactions of the optimized molecules were evaluated by molecular docking methods against BSA “Bovine Serum Albumin” and LIF “Leukemia Inhibitory Factor”. The results obtained from this study will ideally provide a fundamental source in contemporary drug design in terms of both the key electronic properties underlying the possible reactivity features and toxicity.

show abstract

“…However, preparation of cyclobutenes is challenging primarily due to their intrinsic ring strain and inherent tendency to go through electrocyclic ring opening reactions. Despite some progress that has been made, [7] relatively limited substrate scopes [7d–o] and thereby limited applications in natural product synthesis indicate that cyclobutene as a useful building block has still not yet been fully explored. On the other hand, we proposed that the desired [4+2] product could be obtained through the rearrangement of cyclobutene.…”

Section: Figurementioning

confidence: 99%

Concise Synthesis of (±)‐Myrioneurinol Enabled by Sequential [2+2] Cycloaddition/Retro‐Mannich Fragmentation/Mannich Reaction

Zhang

Jiang

2022

Angewandte Chemie

View full text Add to dashboard Cite

A concise total synthesis of (±)‐myrioneurinol has been achieved in 14 steps. An efficient AgSbF6/t‐BuCl‐catalyzed intramolecular [2+2] cycloaddition reaction of the alkynone‐tethered enamine was developed to prepare the highly strained cyclobutene. It was used in combination with a subsequent retro‐Mannich fragmentation/Mannich reaction to efficiently construct the tricyclic core of myrioneurinol.

show abstract

[2+2] Cycloaddition Reactions of Enamines With Electron-Deficient Acetylenes

Cited by 16 publications

References 14 publications

Polycondensation studies of some cycloaddition products bearing carboxylate groups with ethylene glycol

Polycondensation studies of some cycloaddition products bearing carboxylate groups with ethylene glycol

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Concise Synthesis of (±)‐Myrioneurinol Enabled by Sequential [2+2] Cycloaddition/Retro‐Mannich Fragmentation/Mannich Reaction

Contact Info

Product

Resources

About