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N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates
The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding N -alkyl- and N -(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more...
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| Published in: | Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2079-2086 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c316t-38c9acc0eeb6a29eb0899ab977ae31e335819b3f3c2709420986aa6f5d98c8093 |
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| cites | cdi_FETCH-LOGICAL-c316t-38c9acc0eeb6a29eb0899ab977ae31e335819b3f3c2709420986aa6f5d98c8093 |
| container_end_page | 2086 |
| container_issue | 12 |
| container_start_page | 2079 |
| container_title | Russian journal of organic chemistry |
| container_volume | 56 |
| creator | Gabov, I. S. Khamidullina, L. A. Puzyrev, I. S. Ezhikova, M. A. Kodess, M. I. Pestov, A. V. |
| description | The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding
N
-alkyl- and
N
-(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied by DFT quantum chemical calculations at the B3LYP/6-311++G(
d
,
p
) level of theory. |
| doi_str_mv | 10.1134/S1070428020120052 |
| format | article |
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N
-alkyl- and
N
-(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied by DFT quantum chemical calculations at the B3LYP/6-311++G(
d
,
p
) level of theory.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428020120052</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Alkylation ; Carbonates ; Chemistry ; Chemistry and Materials Science ; Ethylene ; Imidazole ; Organic Chemistry ; Quantum chemistry</subject><ispartof>Russian journal of organic chemistry, 2020-12, Vol.56 (12), p.2079-2086</ispartof><rights>Pleiades Publishing, Ltd. 2020</rights><rights>Pleiades Publishing, Ltd. 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-38c9acc0eeb6a29eb0899ab977ae31e335819b3f3c2709420986aa6f5d98c8093</citedby><cites>FETCH-LOGICAL-c316t-38c9acc0eeb6a29eb0899ab977ae31e335819b3f3c2709420986aa6f5d98c8093</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Gabov, I. S.</creatorcontrib><creatorcontrib>Khamidullina, L. A.</creatorcontrib><creatorcontrib>Puzyrev, I. S.</creatorcontrib><creatorcontrib>Ezhikova, M. A.</creatorcontrib><creatorcontrib>Kodess, M. I.</creatorcontrib><creatorcontrib>Pestov, A. V.</creatorcontrib><title>N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding
N
-alkyl- and
N
-(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied by DFT quantum chemical calculations at the B3LYP/6-311++G(
d
,
p
) level of theory.</description><subject>Alkylation</subject><subject>Carbonates</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Ethylene</subject><subject>Imidazole</subject><subject>Organic Chemistry</subject><subject>Quantum chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxYMoWKsfwFvA8-pMku4mJyn1X6HoQT0vs2lWt243Ndki9dObWsGDeJoH7_fewGPsFOEcUaqLR4QClNAgAAXASOyxAeagMymN3E862dnWP2RHMS4AQKGSA3Z5n43bt01LfeM77ms-XTZz-vSti_yj6V_5VUNbn1M359-k6xyfUKh8R72Lx-ygpja6k587ZM8310-Tu2z2cDudjGeZlZj3mdTWkLXgXJWTMK4CbQxVpijISXRSjjSaStbSigKMEmB0TpTXo7nRVoORQ3a2610F_752sS8Xfh269LIUSudYqLRConBH2eBjDK4uV6FZUtiUCOV2p_LPTikjdpmY2O7Fhd_m_0NfPzln2w</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Gabov, I. S.</creator><creator>Khamidullina, L. A.</creator><creator>Puzyrev, I. S.</creator><creator>Ezhikova, M. A.</creator><creator>Kodess, M. I.</creator><creator>Pestov, A. V.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201201</creationdate><title>N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates</title><author>Gabov, I. S. ; Khamidullina, L. A. ; Puzyrev, I. S. ; Ezhikova, M. A. ; Kodess, M. I. ; Pestov, A. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-38c9acc0eeb6a29eb0899ab977ae31e335819b3f3c2709420986aa6f5d98c8093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkylation</topic><topic>Carbonates</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Ethylene</topic><topic>Imidazole</topic><topic>Organic Chemistry</topic><topic>Quantum chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gabov, I. S.</creatorcontrib><creatorcontrib>Khamidullina, L. A.</creatorcontrib><creatorcontrib>Puzyrev, I. S.</creatorcontrib><creatorcontrib>Ezhikova, M. A.</creatorcontrib><creatorcontrib>Kodess, M. I.</creatorcontrib><creatorcontrib>Pestov, A. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gabov, I. S.</au><au>Khamidullina, L. A.</au><au>Puzyrev, I. S.</au><au>Ezhikova, M. A.</au><au>Kodess, M. I.</au><au>Pestov, A. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2020-12-01</date><risdate>2020</risdate><volume>56</volume><issue>12</issue><spage>2079</spage><epage>2086</epage><pages>2079-2086</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding
N
-alkyl- and
N
-(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied by DFT quantum chemical calculations at the B3LYP/6-311++G(
d
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p
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| fulltext | fulltext |
| identifier | ISSN: 1070-4280 |
| ispartof | Russian journal of organic chemistry, 2020-12, Vol.56 (12), p.2079-2086 |
| issn | 1070-4280 1608-3393 |
| language | eng |
| recordid | cdi_proquest_journals_2486174134 |
| source | Springer Nature |
| subjects | Alkylation Carbonates Chemistry Chemistry and Materials Science Ethylene Imidazole Organic Chemistry Quantum chemistry |
| title | N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates |
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