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

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
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Аннотация

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.

Толық мәтін

Рұқсат жабық

Авторлар туралы

L. Klyba

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

Хат алмасуға жауапты Автор.
Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-5521-3201
Ресей, 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
Ресей, 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
Ресей, 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
Ресей, 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
Ресей, 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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