Investigation of the Mechanism of the Alkylation Reaction of 2-Methylimidazole 1,1,3,3-Tetraiodpropane-2-on by the MALDI Method

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Resumo

The mechanism of the alkylation reaction of 2-methylimidazole with 1,1,3,3-tetraiodopropan-2-one in the absence and presence an acceptor (CaCO3) of hydrogen iodide using laser desorption/ionization was studied for the first time. The composition of the reaction mixtures and possible routes for the formation of functionalized 2-methylimidazole derivatives were determined. N1 and N1,3-alkylation of 2-methylimidazole with reduced (1-iodopropan-2-one, 1,3-diiodopropan-2-one) or dehydroiodinated (2,3-diiodo-2-cyclopropen-1) forms 1,1, 3,3-tetraiodoproapan-2-one is a crucial step in the synthesis. The thermodynamic and kinetic characteristics of the reduction and dehydroiodination of 1,1,3,3-tetraiodoacetone were evaluated by quantum-chemical calculations using the [B3LYP/6-311+G(d,p)+dgdzvp) basis set.

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Sobre autores

L. Klyba

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: klyba@irioch.irk.ru
ORCID ID: 0000-0002-5521-3201
Rússia, Favorsky St., 1, Irkutsk, 664033

E. Sanzheeva

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID ID: 0000-0002-9776-2794
Rússia, Favorsky St., 1, Irkutsk, 664033

I. Dorofeev

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID ID: 0000-0003-4646-6554
Rússia, Favorsky St., 1, Irkutsk, 664033

V. Shagun

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID ID: 0000-0002-2189-7043
Rússia, Favorsky St., 1, Irkutsk, 664033

G. Fedorova

Limnological Institute, Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID ID: 0000-0002-1697-8631
Rússia, Ulan-Batorskaya St, 3, Irkutsk, 664033

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2. Fig. 1. The mass spectrum of the MALDI positive ions of reaction mixture I obtained in the reflectron mode using a NALDITM target (Nanosys, Inc. Palo Alto, CA, USA).

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3. Fig. 2. Schematic representation of the reactions of reduction of iodomethyl fragments in 1,1,3,3-tetraiodpropane-2-one (2) during its interaction with hydrogen iodide, according to the calculation method [B3LYP/6-311+G(d,p) + dgdzvp] [29].

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4. Fig. 3. Schematic representation of the elementary stages of formation of formyl iodide (2e) and acetylene, according to the calculation data by the method [B3LYP/6-311+G(d,p) + dgdzvp] [29].

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5. Fig. 4. The molecular structures of the transition states (TS4−TS8) and their corresponding values of the imaginary harmonic frequency, according to the calculation method [B3LYP/6-311+G(d,p) + dgdzvp].

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6. Fig. 5. Mass spectrum of MALDI using a NALDITM target (Nanosys, Inc. Palo Alto, CA, USA) reaction mixture II (alkylation of 2-methylimidazole 1,1,3,3-tetraiodpropane-2-one in the presence of CaCO3).

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7. Scheme 1

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8. Scheme 2

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9. Схема 3

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10. Scheme 4

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11. Scheme 5

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12. Scheme 6

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13. Scheme 7

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14. Scheme 8

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15. Scheme 9

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16. Scheme 10

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17. Scheme 11

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18. Study of the synthetic potential of the alkylation reaction 2-methylimidazole with 1,1,3,3,-tetraiodpropane-2-one by the MALDI method

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