Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamid...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (17), p.6678-6681
Main Authors: Coffin, Aaron R, Roussell, Michael A, Tserlin, Elina, Pelkey, Erin T
Format: Article
Language:English
Subjects:
Amides - chemistry
Chemistry
Cyanides - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993
cites cdi_FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993
container_end_page 6681
container_issue 17
container_start_page 6678
container_title Journal of organic chemistry
container_volume 71
creator Coffin, Aaron R
Roussell, Michael A
Tserlin, Elina
Pelkey, Erin T
description A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.
doi_str_mv 10.1021/jo061043m
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68738545</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68738545</sourcerecordid><originalsourceid>FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993</originalsourceid><addsrcrecordid>eNpt0U1PGzEQBmCralUC5dA_gPbSShxc_LHej2OKGkCKBCWBHi2vPSamuza1NxL59xglkEt9seR5ZjR6jdBXSn5QwujZYyAVJSUfPqAJFYzgqiXlRzQhhDHMWcUP0GFKjyQfIcRndEAzoLSmE7S6hQcXdPBjDH0Pplhs_LiC5FIRbHGzifkZMMNaxS48q97AamMgFcqbguNt3fkMgs-vNobhran4A85H6Irp4HLHF_TJqj7B8e4-QnezX8vzSzy_vrg6n86xKst6xMIYbY2puVG0VYaxxtjKso6DodQaTTpmy6oWJW2EIrzqGKsbAtoQ23bQtvwIfd_OfYrh3xrSKAeXNPS98hDWSVZNzRtRigxPt1DHkFIEK5-iG1TcSErka6zyPdZsT3ZD190AZi93OWbwbQdU0qq3UXnt0t41JP9C--rw1rk0wvN7XcW_sqp5LeTyZiHbi9nvn_e3M3m_n6t0yvuso8_Z_WfBFx3fnAQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68738545</pqid></control><display><type>article</type><title>Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Coffin, Aaron R ; Roussell, Michael A ; Tserlin, Elina ; Pelkey, Erin T</creator><creatorcontrib>Coffin, Aaron R ; Roussell, Michael A ; Tserlin, Elina ; Pelkey, Erin T</creatorcontrib><description>A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo061043m</identifier><identifier>PMID: 16901171</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amides - chemistry ; Chemistry ; Cyanides - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Pyrrolidines - chemical synthesis ; Pyrrolidines - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2006-08, Vol.71 (17), p.6678-6681</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993</citedby><cites>FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=18026391$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16901171$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Coffin, Aaron R</creatorcontrib><creatorcontrib>Roussell, Michael A</creatorcontrib><creatorcontrib>Tserlin, Elina</creatorcontrib><creatorcontrib>Pelkey, Erin T</creatorcontrib><title>Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.</description><subject>Amides - chemistry</subject><subject>Chemistry</subject><subject>Cyanides - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Pyrrolidines - chemical synthesis</subject><subject>Pyrrolidines - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpt0U1PGzEQBmCralUC5dA_gPbSShxc_LHej2OKGkCKBCWBHi2vPSamuza1NxL59xglkEt9seR5ZjR6jdBXSn5QwujZYyAVJSUfPqAJFYzgqiXlRzQhhDHMWcUP0GFKjyQfIcRndEAzoLSmE7S6hQcXdPBjDH0Pplhs_LiC5FIRbHGzifkZMMNaxS48q97AamMgFcqbguNt3fkMgs-vNobhran4A85H6Irp4HLHF_TJqj7B8e4-QnezX8vzSzy_vrg6n86xKst6xMIYbY2puVG0VYaxxtjKso6DodQaTTpmy6oWJW2EIrzqGKsbAtoQ23bQtvwIfd_OfYrh3xrSKAeXNPS98hDWSVZNzRtRigxPt1DHkFIEK5-iG1TcSErka6zyPdZsT3ZD190AZi93OWbwbQdU0qq3UXnt0t41JP9C--rw1rk0wvN7XcW_sqp5LeTyZiHbi9nvn_e3M3m_n6t0yvuso8_Z_WfBFx3fnAQ</recordid><startdate>20060818</startdate><enddate>20060818</enddate><creator>Coffin, Aaron R</creator><creator>Roussell, Michael A</creator><creator>Tserlin, Elina</creator><creator>Pelkey, Erin T</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060818</creationdate><title>Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides</title><author>Coffin, Aaron R ; Roussell, Michael A ; Tserlin, Elina ; Pelkey, Erin T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Amides - chemistry</topic><topic>Chemistry</topic><topic>Cyanides - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Pyrrolidines - chemical synthesis</topic><topic>Pyrrolidines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Coffin, Aaron R</creatorcontrib><creatorcontrib>Roussell, Michael A</creatorcontrib><creatorcontrib>Tserlin, Elina</creatorcontrib><creatorcontrib>Pelkey, Erin T</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Coffin, Aaron R</au><au>Roussell, Michael A</au><au>Tserlin, Elina</au><au>Pelkey, Erin T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-08-18</date><risdate>2006</risdate><volume>71</volume><issue>17</issue><spage>6678</spage><epage>6681</epage><pages>6678-6681</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16901171</pmid><doi>10.1021/jo061043m</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2006-08, Vol.71 (17), p.6678-6681
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_68738545
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Amides - chemistry
Chemistry
Cyanides - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
title Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T10%3A00%3A28IST&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=Regiocontrolled%20Synthesis%20of%20Pyrrole-2-carboxaldehydes%20and%203-Pyrrolin-2-ones%20from%20Pyrrole%20Weinreb%20Amides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Coffin,%20Aaron%20R&rft.date=2006-08-18&rft.volume=71&rft.issue=17&rft.spage=6678&rft.epage=6681&rft.pages=6678-6681&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo061043m&rft_dat=%3Cproquest_cross%3E68738545%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a447t-5ddcfdd73da19ad228df6f2b3ed11fdc0b2f46754185a036b22780ecd0f9be993%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=68738545&rft_id=info:pmid/16901171&rfr_iscdi=true