Synthesis and Structure of Esterification Products of 6-aryl-1,2,3,6,7,7a-hexahydro-3а,6-epoxyisoindole-7-carboxylic Acids

Nadirova, Maryana A.; Pokazeev, Kuzma M.; Kolesnik, I. A.; Dorovatovskii, Pavel V.; Бумагин, Н. А.; Поткин, В. И.

doi:10.1007/s10593-019-02528-z

Cited by 6 publications

(5 citation statements)

References 24 publications

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“…Although IMDAF reactions involving furan systems bearing amide functionality are generally reversible [ 134 ], the formation of the addition products in high yields in this study indicates that the retro- IMDAF reaction does not occur under the reaction conditions developed. As seen in Figure 4b , the different sigma bond lengths formed in the exo transition state (calculations which were performed in Gaussian 16 Rev B.01 (Gaussian, Inc., Wallingford, CT, USA)) [ 135 ] indicate that the IMDAF reaction proceeds through an asynchronous process (the same is true for the endo transition state).…”

Section: Resultsmentioning

confidence: 78%

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Yıldırım

2024

Beilstein J. Org. Chem.

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Tandem Diels–Alder reactions are often used for the straightforward formation of complex natural compounds and the fused polycyclic systems contained in their precursors. In the second step of this reaction, regio- and stereochemically controlled intramolecular cyclization leads to the formation of versatile nitrogen-containing tricyclic systems. However, these useful organic transformations are usually carried out in highly toxic organic solvents such as benzene, toluene, chloroform, etc. Despite recent efforts by 'green chemists', synthetic chemists still use these traditional toxic organic solvents in many of their reactions, even though safer alternatives are available. However, in addition to the harmful effects of these petrochemical solvents on the environment, the prediction that their resources will run out in the near future has led 'green chemists' to explore solvents that can be derived from renewable resources and used effectively in various organic transformations. In this context, we have shown for the first time that the 100% atom-economical tandem Diels–Alder reaction between aminofuranes and maleic anhydride can be carried out successfully in vegetable oils and waxes. The reaction was successfully carried out in sunflower seed oil, olive oil, oleic acid and lauryl myristate under mild reaction conditions. A series of epoxyisoindole-7-carboxylic acid and bisepoxyisoindole-7-carboxylic acids were obtained in good yields after a practical isolation procedure. The results obtained in this study demonstrate the potential of vegetable oils and their renewable materials to provide a reaction medium that is more sustainable than conventional organic solvents in cascade Diels–Alder reactions and can be used repeatedly without significant degradation. These materials also allow the reaction to be completed in less time, with less energy consumption and higher yields.

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Section: Resultsmentioning

confidence: 78%

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Yıldırım

2024

Beilstein J. Org. Chem.

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“…Isoindoles are important structural units of many natural products and are widely used as drugs and as building blocks for the construction of new N-containing heterocyclic compounds or functional materials (Nadirova et al, 2019;Zubkov et al, 2011Zubkov et al, , 2014Zubkov et al, , 2018. The biological and physical properties of isoindoles depend on the attached functional groups (Krishna et al, 2021;Zaytsev et al, 2017Zaytsev et al, , 2019Zaytsev et al, , 2020.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-2-(4-methoxyphenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,6-epoxy-1H-cyclopenta[c]pyridin-1-one

et al. 2021

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The molecule of the title compound, C15H15Br2NO3, comprises a fused tricyclic system consisting of two five-membered rings (cyclopentane and tetrahydrofuran) and one six-membered ring (tetrahydropyridinone). Both five-membered rings of the tricyclic system have envelope conformations, and the conformation of the six-membered cycle is intermediate between chair and half-chair. In the crystal, the molecules are linked by C—H...O hydrogen bonds and C—H...π, C—Br...π and C...O interactions into double layers. The layers are connected into a three-dimensional network by van der Waals interactions.

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“…On the other hand, the isoindole synthon is an important structural unit in many natural products and bioactive compounds, as well as a useful building-block for the construction of new N-containing heterocyclic compounds [27][28][29][30][31][32][33][34]. For instance, heterocyclic compounds containing isoindole moieties have demonstrated a promising biological action and pharmacological activity as pathogen antagonists [29].…”

Section: Introductionmentioning

confidence: 99%

“…For instance, heterocyclic compounds containing isoindole moieties have demonstrated a promising biological action and pharmacological activity as pathogen antagonists [29]. The isoindole motif can also be involved as a versatile and powerful intermediate for the synthesis of various chiral heterocyclic compounds with unique properties [27][28][29][30][31][32][33][34]. Thus, the functionalization of isoindole moieties with noncovalent bond donor/acceptor sites can improve their photophysical properties [27], bioactivity [32], coordination ability [35,36], etc.…”

Section: Introductionmentioning

confidence: 99%

Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones

et al. 2021

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A series of 4,5-dibromo-2-(4-substituted phenyl)hexahydro-3a,6-epoxyisoindol-1(4H)-ones were synthesized by reaction of the corresponding 2-(4-substituted phenyl)-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-ones with [(Me2NCOMe)2H]Br3 in dry chloroform under reflux for 3−5 h. In contrast to the 4-F and 4-Cl substituents, one of the bromine atoms of the isoindole moiety behaves as a halogen bond donor in the formation of intermolecular halogen bonding in the 4-H, 4-Br and 4-I analogues. Not only intermolecular hydrogen bonds, but also Ha⋯Ha and Ha⋯π types of halogen bonds in the 4-H, 4-Br, and 4-I compounds, contribute to the formation of supramolecular architectures leading to 2D or 3D structures.

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Synthesis and Structure of Esterification Products of 6-aryl-1,2,3,6,7,7a-hexahydro-3а,6-epoxyisoindole-7-carboxylic Acids

Cited by 6 publications

References 24 publications

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-2-(4-methoxyphenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,6-epoxy-1H-cyclopenta[c]pyridin-1-one

Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones

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