Loading…

A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides

An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the prese...

Full description

Saved in:

Bibliographic Details
Published in:	Tetrahedron letters 2011-06, Vol.52 (26), p.3287-3290
Main Authors:	Majce, Vita, Kočevar, Marijan, Polanc, Slovenko
Format:	Article
Language:	English
Subjects:	Acetonitrile Aliphatic compounds Amine catalysis Chemistry Exact sciences and technology Fumaramides Fumaric acid Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Isomerization Kinetics and mechanisms Microwave irradiation Microwaves Organic chemistry Preparations and properties Reactivity and mechanisms Reactors Solvents Synthesis (chemistry) Tetrahedrons
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-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3
cites	cdi_FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3
container_end_page	3290
container_issue	26
container_start_page	3287
container_title	Tetrahedron letters
container_volume	52
creator	Majce, Vita Kočevar, Marijan Polanc, Slovenko
description	An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.
doi_str_mv	10.1016/j.tetlet.2011.04.066
format	article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744677737</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403911006496</els_id><sourcerecordid>1744677737</sourcerecordid><originalsourceid>FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3</originalsourceid><addsrcrecordid>eNp9UE1r3DAQFSWFbLf9BznoUujFrmTJln0phCVpCwu5pGcxlsagxR9bjTZl8-ujxUuPmcsMj_fmzTzG7qQopZDN90OZMI2YykpIWQpdiqb5wDayNapQdStv2EYILQotVHfLPhEdRK6mFRvW3_MIx-A5zJ5TmI4jcpjCjIWDBOP5FT2fgovLP3jBAogCpQwFWiaM4RVSWGa-DHyCEbPOI_Ewp4UPpwniCnxmHwcYCb9c-5b9eXx43v0q9k8_f-_u94VTTZeKVmIvvdD9AL3zKLSHSklXdwqgqs3Q9Iit7nRX-w40oO-N6fNcK131g0G1Zd_Wvce4_D0hJTsFcjiOMONyIiuN1o0xRplM1Ss1P0YUcbDHGPLBZyuFvURqD3aN1F4itULbHGmWfb06ADkYhwizC_RfW-lKdVWtM-_HysP87kvAaMkFnB36ENEl65fwvtEbfaORNQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744677737</pqid></control><display><type>article</type><title>A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides</title><source>ScienceDirect Freedom Collection</source><creator>Majce, Vita ; Kočevar, Marijan ; Polanc, Slovenko</creator><creatorcontrib>Majce, Vita ; Kočevar, Marijan ; Polanc, Slovenko</creatorcontrib><description>An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2011.04.066</identifier><identifier>CODEN: TELEAY</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Acetonitrile ; Aliphatic compounds ; Amine catalysis ; Chemistry ; Exact sciences and technology ; Fumaramides ; Fumaric acid ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Isomerization ; Kinetics and mechanisms ; Microwave irradiation ; Microwaves ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms ; Reactors ; Solvents ; Synthesis (chemistry) ; Tetrahedrons</subject><ispartof>Tetrahedron letters, 2011-06, Vol.52 (26), p.3287-3290</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3</citedby><cites>FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24239254$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Majce, Vita</creatorcontrib><creatorcontrib>Kočevar, Marijan</creatorcontrib><creatorcontrib>Polanc, Slovenko</creatorcontrib><title>A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides</title><title>Tetrahedron letters</title><description>An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.</description><subject>Acetonitrile</subject><subject>Aliphatic compounds</subject><subject>Amine catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fumaramides</subject><subject>Fumaric acid</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Isomerization</subject><subject>Kinetics and mechanisms</subject><subject>Microwave irradiation</subject><subject>Microwaves</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Reactors</subject><subject>Solvents</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9UE1r3DAQFSWFbLf9BznoUujFrmTJln0phCVpCwu5pGcxlsagxR9bjTZl8-ujxUuPmcsMj_fmzTzG7qQopZDN90OZMI2YykpIWQpdiqb5wDayNapQdStv2EYILQotVHfLPhEdRK6mFRvW3_MIx-A5zJ5TmI4jcpjCjIWDBOP5FT2fgovLP3jBAogCpQwFWiaM4RVSWGa-DHyCEbPOI_Ewp4UPpwniCnxmHwcYCb9c-5b9eXx43v0q9k8_f-_u94VTTZeKVmIvvdD9AL3zKLSHSklXdwqgqs3Q9Iit7nRX-w40oO-N6fNcK131g0G1Zd_Wvce4_D0hJTsFcjiOMONyIiuN1o0xRplM1Ss1P0YUcbDHGPLBZyuFvURqD3aN1F4itULbHGmWfb06ADkYhwizC_RfW-lKdVWtM-_HysP87kvAaMkFnB36ENEl65fwvtEbfaORNQ</recordid><startdate>20110629</startdate><enddate>20110629</enddate><creator>Majce, Vita</creator><creator>Kočevar, Marijan</creator><creator>Polanc, Slovenko</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110629</creationdate><title>A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides</title><author>Majce, Vita ; Kočevar, Marijan ; Polanc, Slovenko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acetonitrile</topic><topic>Aliphatic compounds</topic><topic>Amine catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Fumaramides</topic><topic>Fumaric acid</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Isomerization</topic><topic>Kinetics and mechanisms</topic><topic>Microwave irradiation</topic><topic>Microwaves</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Reactors</topic><topic>Solvents</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Majce, Vita</creatorcontrib><creatorcontrib>Kočevar, Marijan</creatorcontrib><creatorcontrib>Polanc, Slovenko</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Majce, Vita</au><au>Kočevar, Marijan</au><au>Polanc, Slovenko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides</atitle><jtitle>Tetrahedron letters</jtitle><date>2011-06-29</date><risdate>2011</risdate><volume>52</volume><issue>26</issue><spage>3287</spage><epage>3290</epage><pages>3287-3290</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><coden>TELEAY</coden><abstract>An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.04.066</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0040-4039
ispartof	Tetrahedron letters, 2011-06, Vol.52 (26), p.3287-3290
issn	0040-4039 1873-3581
language	eng
recordid	cdi_proquest_miscellaneous_1744677737
source	ScienceDirect Freedom Collection
subjects	Acetonitrile Aliphatic compounds Amine catalysis Chemistry Exact sciences and technology Fumaramides Fumaric acid Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Isomerization Kinetics and mechanisms Microwave irradiation Microwaves Organic chemistry Preparations and properties Reactivity and mechanisms Reactors Solvents Synthesis (chemistry) Tetrahedrons
title	A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides
url	http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T23%3A02%3A47IST&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=A%20rapid%20and%20simple%20amine-catalyzed%20microwave-assisted%20isomerization%20of%20maleamides%20into%20fumaramides&rft.jtitle=Tetrahedron%20letters&rft.au=Majce,%20Vita&rft.date=2011-06-29&rft.volume=52&rft.issue=26&rft.spage=3287&rft.epage=3290&rft.pages=3287-3290&rft.issn=0040-4039&rft.eissn=1873-3581&rft.coden=TELEAY&rft_id=info:doi/10.1016/j.tetlet.2011.04.066&rft_dat=%3Cproquest_cross%3E1744677737%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c369t-81eb1d04bfabcde04da231c593aa257f6bee849495d9a4aedb77b5d95342bf7e3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1744677737&rft_id=info:pmid/&rfr_iscdi=true