A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes
2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various sub...
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| Veröffentlicht in: | New journal of chemistry 2018, Vol.42 (5), p.326-3269 |
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| container_issue | 5 |
| container_start_page | 326 |
| container_title | New journal of chemistry |
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| creator | Bujok, Robert Wiszniewski, Marcin Cmoch, Piotr Wróbel, Zbigniew |
| description | 2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various substituents in the 2-position. Starting from non-racemic aldehydes, non-racemic 2-substituted 6-nitroindoles were obtained.
Starting from 2,4-dinitrotoluene and aldehydes, 2-substituted 6-nitroindoles with alkyl, cycloalkyl, aryl and heteroaryl (thienyl, furyl, pyridyl) substituents in the 2-position of the indole ring were synthesized. This methodology can be used for synthesis of indoles with non-racemic substituents. |
| doi_str_mv | 10.1039/c7nj04919f |
| format | Article |
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Starting from 2,4-dinitrotoluene and aldehydes, 2-substituted 6-nitroindoles with alkyl, cycloalkyl, aryl and heteroaryl (thienyl, furyl, pyridyl) substituents in the 2-position of the indole ring were synthesized. This methodology can be used for synthesis of indoles with non-racemic substituents.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/c7nj04919f</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alcohol ; Alcohols ; Aldehydes ; Catalysis ; Ketones ; Substitutes ; Synthesis</subject><ispartof>New journal of chemistry, 2018, Vol.42 (5), p.326-3269</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-b2ecbc71f562777610d24688c9e7b3a522025db1f8a7d912012944274657fcca3</citedby><cites>FETCH-LOGICAL-c281t-b2ecbc71f562777610d24688c9e7b3a522025db1f8a7d912012944274657fcca3</cites><orcidid>0000-0002-9609-7067 ; 0000-0001-5971-6992 ; 0000-0002-8413-9290 ; 0000-0002-4633-9304</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Bujok, Robert</creatorcontrib><creatorcontrib>Wiszniewski, Marcin</creatorcontrib><creatorcontrib>Cmoch, Piotr</creatorcontrib><creatorcontrib>Wróbel, Zbigniew</creatorcontrib><title>A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes</title><title>New journal of chemistry</title><description>2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various substituents in the 2-position. Starting from non-racemic aldehydes, non-racemic 2-substituted 6-nitroindoles were obtained.
Starting from 2,4-dinitrotoluene and aldehydes, 2-substituted 6-nitroindoles with alkyl, cycloalkyl, aryl and heteroaryl (thienyl, furyl, pyridyl) substituents in the 2-position of the indole ring were synthesized. This methodology can be used for synthesis of indoles with non-racemic substituents.</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Catalysis</subject><subject>Ketones</subject><subject>Substitutes</subject><subject>Synthesis</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpNkcFO3DAQhiNUJOjSS--VLPVWkcV2nDg5rlZQQAgucI4ce9z1NrGpx6m0vBPvWLNbtZxmNPpm5p_5i-Izo0tGq-5CS7-lomOdPSpOWdV0Zccb9iHnTIiS1qI5KT4ibillTDbstHhdkR_gIaqRKG-IDv43eAc-kQnSJhhiQyRpAwR3Pgd0SIIl_FyUxnmXYhjAv-xG8hNS8IBLshqngInMfnSTS2CI0hoQSQqElzgPmFya3-pNue933oQRkNgYpvdzUxjnLGyvSo0GNjsDeFYcWzUifPobF8XT1eXj-rq8e_h-s17dlZq3LJUDBz1oyWzdcCnzndRw0bSt7kAOlao5p7w2A7OtkqZjnDLeCcGlaGpptVbVovh6mPscw68ZMPXbMEefV_YZpq3k-ZOZ-nagdAyIEWz_HN2k4q5ntH-zo1_L-9u9HVcZ_nKAI-p_3H-7qj_ST4lK</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Bujok, Robert</creator><creator>Wiszniewski, Marcin</creator><creator>Cmoch, Piotr</creator><creator>Wróbel, Zbigniew</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0002-9609-7067</orcidid><orcidid>https://orcid.org/0000-0001-5971-6992</orcidid><orcidid>https://orcid.org/0000-0002-8413-9290</orcidid><orcidid>https://orcid.org/0000-0002-4633-9304</orcidid></search><sort><creationdate>2018</creationdate><title>A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes</title><author>Bujok, Robert ; Wiszniewski, Marcin ; Cmoch, Piotr ; Wróbel, Zbigniew</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-b2ecbc71f562777610d24688c9e7b3a522025db1f8a7d912012944274657fcca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Catalysis</topic><topic>Ketones</topic><topic>Substitutes</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bujok, Robert</creatorcontrib><creatorcontrib>Wiszniewski, Marcin</creatorcontrib><creatorcontrib>Cmoch, Piotr</creatorcontrib><creatorcontrib>Wróbel, Zbigniew</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bujok, Robert</au><au>Wiszniewski, Marcin</au><au>Cmoch, Piotr</au><au>Wróbel, Zbigniew</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes</atitle><jtitle>New journal of chemistry</jtitle><date>2018</date><risdate>2018</risdate><volume>42</volume><issue>5</issue><spage>326</spage><epage>3269</epage><pages>326-3269</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various substituents in the 2-position. Starting from non-racemic aldehydes, non-racemic 2-substituted 6-nitroindoles were obtained.
Starting from 2,4-dinitrotoluene and aldehydes, 2-substituted 6-nitroindoles with alkyl, cycloalkyl, aryl and heteroaryl (thienyl, furyl, pyridyl) substituents in the 2-position of the indole ring were synthesized. This methodology can be used for synthesis of indoles with non-racemic substituents.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c7nj04919f</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-9609-7067</orcidid><orcidid>https://orcid.org/0000-0001-5971-6992</orcidid><orcidid>https://orcid.org/0000-0002-8413-9290</orcidid><orcidid>https://orcid.org/0000-0002-4633-9304</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2018, Vol.42 (5), p.326-3269 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_rsc_primary_c7nj04919f |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohol Alcohols Aldehydes Catalysis Ketones Substitutes Synthesis |
| title | A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes |
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