Synthesis and properties of new heterocyclic betaines: 4-Aryl-5(methoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH- pyrrol-3-ides

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Abstract

New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2466-2474
Number of pages9
JournalTetrahedron
Volume74
Issue number20
DOIs
Publication statusPublished - 17 May 2018

Cite this

@article{5fb471a4b0124123b0474ed9dab903c4,
title = "Synthesis and properties of new heterocyclic betaines: 4-Aryl-5(methoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH- pyrrol-3-ides",
abstract = "New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.",
keywords = "Heterocyclic betaines, Azirines, Pyridinium ylides, Solvatochromism, MESOMERIC BETAINES, PYRIDINIUM YLIDES, DENSITY, CARBENES, EXCHANGE, SALTS, TAUTOMERIZATION, THERMOCHEMISTRY, CYCLOADDITION, DERIVATIVES",
author = "Funt, {Liya D.} and Novikov, {Mikhail S.} and Starova, {Galina L.} and Khlebnikov, {Alexander F.}",
year = "2018",
month = "5",
day = "17",
doi = "10.1016/j.tet.2018.03.071",
language = "Английский",
volume = "74",
pages = "2466--2474",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "20",

}

TY - JOUR

T1 - Synthesis and properties of new heterocyclic betaines

T2 - 4-Aryl-5(methoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH- pyrrol-3-ides

AU - Funt, Liya D.

AU - Novikov, Mikhail S.

AU - Starova, Galina L.

AU - Khlebnikov, Alexander F.

PY - 2018/5/17

Y1 - 2018/5/17

N2 - New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.

AB - New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.

KW - Heterocyclic betaines

KW - Azirines

KW - Pyridinium ylides

KW - Solvatochromism

KW - MESOMERIC BETAINES

KW - PYRIDINIUM YLIDES

KW - DENSITY

KW - CARBENES

KW - EXCHANGE

KW - SALTS

KW - TAUTOMERIZATION

KW - THERMOCHEMISTRY

KW - CYCLOADDITION

KW - DERIVATIVES

U2 - 10.1016/j.tet.2018.03.071

DO - 10.1016/j.tet.2018.03.071

M3 - статья

VL - 74

SP - 2466

EP - 2474

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -