Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation
A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with co...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2011-04, Vol.76 (8), p.2860-2866 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2866 |
|---|---|
| container_issue | 8 |
| container_start_page | 2860 |
| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Attanasi, Orazio A Favi, Gianfranco Mantellini, Fabio Moscatelli, Giada Santeusanio, Stefania |
| description | A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles. |
| doi_str_mv | 10.1021/jo200287k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_861587345</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>861587345</sourcerecordid><originalsourceid>FETCH-LOGICAL-a410t-8ef473ec378b2c886ed1b801eb7bab009823adf657c8dcbb469d9d3241fa26263</originalsourceid><addsrcrecordid>eNptkM9u1DAQxi1URJfCoS-AfKkQh4D_JI5zXK26gFQJpC3naOJMVLeOvbWTlXafgDOPyJPgqkvh0LmM5tNP38x8hJxz9pEzwT_dBsGY0PXdC7LglWCFalh5QhZZFIUUSp6S1yndslxVVb0ip4LLphJNvSCHzd5PN5hsomGg69mbyQYPzh6wp9_3MQaHie4s0BVM4PZpKij4nm6C26GfinVEpBu8n_NgwdHrmywUqzBug88SvfQwWo-_f_5aHgJ6pEvvZwcPS96QlwO4hG-P_Yz8WF9er74UV98-f10trwooOZsKjUNZSzSy1p0wWivseacZx67uoGOs0UJCP6iqNro3XVeqpm96KUo-gFD5-TPy_tF3G0O-M03taJNB58BjmFOrFa90Lcsqkx8eSRNDShGHdhvtCHHfctY-JN0-JZ3Zd0fXuRuxfyL_RpuBiyMAyYAbInhj0z-uZEpJ_R8HJmX_Oeb00zML_wDt2ZTR</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>861587345</pqid></control><display><type>article</type><title>Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation</title><source>ACS Publications</source><creator>Attanasi, Orazio A ; Favi, Gianfranco ; Mantellini, Fabio ; Moscatelli, Giada ; Santeusanio, Stefania</creator><creatorcontrib>Attanasi, Orazio A ; Favi, Gianfranco ; Mantellini, Fabio ; Moscatelli, Giada ; Santeusanio, Stefania</creatorcontrib><description>A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo200287k</identifier><identifier>PMID: 21395297</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Journal of organic chemistry, 2011-04, Vol.76 (8), p.2860-2866</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-8ef473ec378b2c886ed1b801eb7bab009823adf657c8dcbb469d9d3241fa26263</citedby><cites>FETCH-LOGICAL-a410t-8ef473ec378b2c886ed1b801eb7bab009823adf657c8dcbb469d9d3241fa26263</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo200287k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo200287k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24066387$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21395297$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Attanasi, Orazio A</creatorcontrib><creatorcontrib>Favi, Gianfranco</creatorcontrib><creatorcontrib>Mantellini, Fabio</creatorcontrib><creatorcontrib>Moscatelli, Giada</creatorcontrib><creatorcontrib>Santeusanio, Stefania</creatorcontrib><title>Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.</description><subject>Aliphatic compounds</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNptkM9u1DAQxi1URJfCoS-AfKkQh4D_JI5zXK26gFQJpC3naOJMVLeOvbWTlXafgDOPyJPgqkvh0LmM5tNP38x8hJxz9pEzwT_dBsGY0PXdC7LglWCFalh5QhZZFIUUSp6S1yndslxVVb0ip4LLphJNvSCHzd5PN5hsomGg69mbyQYPzh6wp9_3MQaHie4s0BVM4PZpKij4nm6C26GfinVEpBu8n_NgwdHrmywUqzBug88SvfQwWo-_f_5aHgJ6pEvvZwcPS96QlwO4hG-P_Yz8WF9er74UV98-f10trwooOZsKjUNZSzSy1p0wWivseacZx67uoGOs0UJCP6iqNro3XVeqpm96KUo-gFD5-TPy_tF3G0O-M03taJNB58BjmFOrFa90Lcsqkx8eSRNDShGHdhvtCHHfctY-JN0-JZ3Zd0fXuRuxfyL_RpuBiyMAyYAbInhj0z-uZEpJ_R8HJmX_Oeb00zML_wDt2ZTR</recordid><startdate>20110415</startdate><enddate>20110415</enddate><creator>Attanasi, Orazio A</creator><creator>Favi, Gianfranco</creator><creator>Mantellini, Fabio</creator><creator>Moscatelli, Giada</creator><creator>Santeusanio, Stefania</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110415</creationdate><title>Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation</title><author>Attanasi, Orazio A ; Favi, Gianfranco ; Mantellini, Fabio ; Moscatelli, Giada ; Santeusanio, Stefania</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-8ef473ec378b2c886ed1b801eb7bab009823adf657c8dcbb469d9d3241fa26263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aliphatic compounds</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Attanasi, Orazio A</creatorcontrib><creatorcontrib>Favi, Gianfranco</creatorcontrib><creatorcontrib>Mantellini, Fabio</creatorcontrib><creatorcontrib>Moscatelli, Giada</creatorcontrib><creatorcontrib>Santeusanio, Stefania</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Attanasi, Orazio A</au><au>Favi, Gianfranco</au><au>Mantellini, Fabio</au><au>Moscatelli, Giada</au><au>Santeusanio, Stefania</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-04-15</date><risdate>2011</risdate><volume>76</volume><issue>8</issue><spage>2860</spage><epage>2866</epage><pages>2860-2866</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21395297</pmid><doi>10.1021/jo200287k</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2011-04, Vol.76 (8), p.2860-2866 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_861587345 |
| source | ACS Publications |
| subjects | Aliphatic compounds Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine−Azoene Annulation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T11%3A37%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Functionalized%20Pyrroles%20via%20Catalyst-%20and%20Solvent-Free%20Sequential%20Three-Component%20Enamine%E2%88%92Azoene%20Annulation&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Attanasi,%20Orazio%20A&rft.date=2011-04-15&rft.volume=76&rft.issue=8&rft.spage=2860&rft.epage=2866&rft.pages=2860-2866&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo200287k&rft_dat=%3Cproquest_cross%3E861587345%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=861587345&rft_id=info:pmid/21395297&rfr_iscdi=true |