ChemInform Abstract: A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)‐Furanone Moieties.

Малькина, А. Г.; Shemyakina, Olesya A.; Степанов, А. В.; Volostnykh, O. G.; Ushakov, Igor А.; Собенина, Л. Н.; Bоrodinа, Tatyana N.; Смирнов, В. И.; Трофимов, Б. А.

doi:10.1002/chin.201623044

Cited by 4 publications

(11 citation statements)

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“…Cyanoacetylenic alcohols 1a-c readily reacted with pyrrole-2carboxylic acids 34a-e in Et3N/MeCN system to afford pyrrole-3(2H)-furanones 35a-m (Scheme 28). 60 Scheme 28 Synthesis of pyrrole-3(2Н)-furanone derivatives 35 from cyanoacetylenic alcohols 1 and pyrrole-2-carboxylic acids 34 60 The reaction between tetrahydroindole-2-carboxylic acid 36 and indole-2-carboxylic acid 37 and cyanoacetylenic alcohols 1 afforded indol-3(2Н)-furanones 38a-c, 39 (Scheme 29). 60 Scheme 29 Synthesis of tetrahydroindol-and indol-3(2Н)-furanone derivatives 38, 39…”

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

“…the 2:1 adducts 40 (Scheme 30). 61 Scheme 30 A cyclization of cyanoacetylenic alcohols with carboxylic acids to 2:1 adducts 40…”

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

“…A further investigation showed that 2:1 adduct 40a became a major product (52%), while the yield of 1:1 adduct 35k dropped from 91% (Scheme 28) to 35% (Scheme 31). 61 Scheme 31 2:1 Cyclization of cyanoacetylenic alcohols 1 and 1H-pyrrole-2carboxylic acid 34e…”

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

“…Note that the competing adducts 35k and 40a were obtained in 24 and 30% yields (Scheme 32). 61 Scheme 32 Formation of the intermediate 41a from cyanoacetylenic alcohol 1a and pyrrole-2-carboxylic acid 34e…”

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

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Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Трофимов¹,

Малькина²

2021

Synthesis

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Cyanoacetylenic alcohols, R1R2C(OH)C≡C-CN, the closest derivatives of cyanoacetylene, an interstellar abundant molecule, are now becoming acknowledgeable in modern organic synthesis which tends to mimic nature. Highly reactive C≡C and C≡N bonds in close vicinity of the hydroxyl group makes these molecules a chemical trinity of mutually influencing functions ensuring an endless number of chemical transformations. All reactions of cyanoacetylenic alcohols parallel modern organic synthesis, being biomimetic. They do not need transition metals (and in most cases, the metals at all except for physiologically indispensible Na+, K+), proceed at ambient temperature and often in aqueous media. Fundamentally, these reactions are 100% atom-economic because they are almost exclusively addition processes. Usually, in the cyanoacetylenic alcohols, cyano, acetylene and hydroxyl functions behave as inseparable entity providing the multiple functionalizations of the forming molecules. This allows hydroxyl, carbonyl, carboxylic, imino, amino, amido, cyanoamido, cyano, various P-containing, ether and ester functions, along with the double bonds and different fundamental heterocycles (furans, furanones, pyrazoles, oxazoles, pyridines, pyrimidines, purins, etc.) and diverse polycyclic systems to be integrated in a one molecular architecture. This review focuses on analysis and generalization of the knowledge accumulated in the chemistry of these cyanoacetylenic alcohols, mostly over the past 15 years.

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Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

“…the 2:1 adducts 40 (Scheme 30). 61 Scheme 30 A cyclization of cyanoacetylenic alcohols with carboxylic acids to 2:1 adducts 40…”

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

Section: Pyrrole-and Indole-2-carboxylic Acidmentioning

confidence: 99%

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Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Трофимов¹,

Малькина²

2021

Synthesis

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“…Many chemical transformations and rearrangements of diverse imines (in particular, oximes) utilized in the synthesis of azoles and larger nitrogen‐containing heterocycles (see classical paper by Trofimov and Mikhaleva together with some more recent contributions from this team) occur stereoselectively, which makes the problem of stereoelectronic effects at the C═N bond to be of crucial importance. In this connection, our earlier and later experimental and theoretical studies of imines received a new impact, especially in line with the recent breakthrough in the NMR‐oriented theory and computation including, in particular, general computational approaches for 15 N NMR chemical shifts …”

Section: Introductionmentioning

confidence: 99%

GIAO‐DFT calculation of ¹⁵N NMR chemical shifts of Schiff bases: Accuracy factors and protonation effects

Semenov

Samultsev

Krivdin

2018

Magnetic Reson in Chemistry

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N NMR chemical shifts in the representative series of Schiff bases together with their protonated forms have been calculated at the density functional theory level in comparison with available experiment. A number of functionals and basis sets have been tested in terms of a better agreement with experiment. Complimentary to gas phase results, 2 solvation models, namely, a classical Tomasi's polarizable continuum model (PCM) and that in combination with an explicit inclusion of one molecule of solvent into calculation space to form supermolecule 1:1 (SM + PCM), were examined. Best results are achieved with PCM and SM + PCM models resulting in mean absolute errors of calculated N NMR chemical shifts in the whole series of neutral and protonated Schiff bases of accordingly 5.2 and 5.8 ppm as compared with 15.2 ppm in gas phase for the range of about 200 ppm. Noticeable protonation effects (exceeding 100 ppm) in protonated Schiff bases are rationalized in terms of a general natural bond orbital approach.

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Synthesis of 4-Halo-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

et al. 2017

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ChemInform Abstract: A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)‐Furanone Moieties.

Cited by 4 publications

References 1 publication

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

GIAO‐DFT calculation of ¹⁵N NMR chemical shifts of Schiff bases: Accuracy factors and protonation effects

Synthesis of 4-Halo-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

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ChemInform Abstract: A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)‐Furanone Moieties.

Cited by 4 publications

References 1 publication

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

GIAO‐DFT calculation of 15N NMR chemical shifts of Schiff bases: Accuracy factors and protonation effects

Synthesis of 4-Halo-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

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Product

Resources

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GIAO‐DFT calculation of ¹⁵N NMR chemical shifts of Schiff bases: Accuracy factors and protonation effects