One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions

In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile)...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Tetrahedron 2014-12, Vol.70 (50), p.9512-9521
Hauptverfasser: Rahmati, Abbas, Ahmadi, Samaneh, Ahmadi-Varzaneh, Mahdi
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9521
container_issue 50
container_start_page 9512
container_title Tetrahedron
container_volume 70
creator Rahmati, Abbas
Ahmadi, Samaneh
Ahmadi-Varzaneh, Mahdi
description In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile) in CH2Cl2 at ambient temperature. Synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine proceeded via four- and five-component reactions; while the synthesis of malonamide derivatives was performed using five- and six-component reactions. In addition, a new series of the malonamide derivatives have been prepared using an aldehyde, malononitrile, Meldrum's acid, an isocyanide, and two molecules of 1,4-diamine via a six-component reaction. These procedures provide alternative methods to the synthesis of a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives. [Display omitted]
doi_str_mv 10.1016/j.tet.2014.10.060
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744682854</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402014015117</els_id><sourcerecordid>1744682854</sourcerecordid><originalsourceid>FETCH-LOGICAL-c330t-fc06999d9e512c56b12942e921ed0bbd360907e3fddaf57237d9e57b9e3ad8303</originalsourceid><addsrcrecordid>eNp9kE9rGzEUxEVJoU7aD5Cbjj1Y7tOf3fWSUwltUgjk0p5MEFrpbSOzK20k2cQ-9pNnjXPu6THDzMD7EXLNYcWB19-2q4JlJYCrWa-ghg9kwVWtWKV4fUEWAAqYAgGfyGXOWwDgXMgF-fcYkE2x0HwI5RmzzzT2lC_FUi0rNm8m83xwKbLZYM7H19hhOMZN97ThS_XkvDni5ANSExwdzRCDGb1D6jD5vSl-j5nusg9_6bgbimc2jlMMGApNaGzxMeTP5GNvhoxf3u8V-fPzx-_be_bwePfr9vsDs1JCYb2Fum1b12LFha3qjotWCWwFRwdd52QNLTQoe-dMXzVCNqdo07UojVtLkFfk63l3SvFlh7no0WeLw2ACxl3WvFGqXot1peYoP0dtijkn7PWU_GjSQXPQJ956q2c2-sT7ZM28587NuYPzD3uPSWfrMVh0PqEt2kX_n_YbWVSJvQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744682854</pqid></control><display><type>article</type><title>One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions</title><source>Access via ScienceDirect (Elsevier)</source><creator>Rahmati, Abbas ; Ahmadi, Samaneh ; Ahmadi-Varzaneh, Mahdi</creator><creatorcontrib>Rahmati, Abbas ; Ahmadi, Samaneh ; Ahmadi-Varzaneh, Mahdi</creatorcontrib><description>In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile) in CH2Cl2 at ambient temperature. Synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine proceeded via four- and five-component reactions; while the synthesis of malonamide derivatives was performed using five- and six-component reactions. In addition, a new series of the malonamide derivatives have been prepared using an aldehyde, malononitrile, Meldrum's acid, an isocyanide, and two molecules of 1,4-diamine via a six-component reaction. These procedures provide alternative methods to the synthesis of a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives. [Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2014.10.060</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Aldehydes ; Ambient temperature ; Derivatives ; Diazepines ; Malonamides ; Malononitrile ; Multi-component condensation reaction ; Synthesis (chemistry) ; Tetrahedrons</subject><ispartof>Tetrahedron, 2014-12, Vol.70 (50), p.9512-9521</ispartof><rights>2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c330t-fc06999d9e512c56b12942e921ed0bbd360907e3fddaf57237d9e57b9e3ad8303</citedby><cites>FETCH-LOGICAL-c330t-fc06999d9e512c56b12942e921ed0bbd360907e3fddaf57237d9e57b9e3ad8303</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2014.10.060$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Rahmati, Abbas</creatorcontrib><creatorcontrib>Ahmadi, Samaneh</creatorcontrib><creatorcontrib>Ahmadi-Varzaneh, Mahdi</creatorcontrib><title>One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions</title><title>Tetrahedron</title><description>In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile) in CH2Cl2 at ambient temperature. Synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine proceeded via four- and five-component reactions; while the synthesis of malonamide derivatives was performed using five- and six-component reactions. In addition, a new series of the malonamide derivatives have been prepared using an aldehyde, malononitrile, Meldrum's acid, an isocyanide, and two molecules of 1,4-diamine via a six-component reaction. These procedures provide alternative methods to the synthesis of a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives. [Display omitted]</description><subject>Aldehydes</subject><subject>Ambient temperature</subject><subject>Derivatives</subject><subject>Diazepines</subject><subject>Malonamides</subject><subject>Malononitrile</subject><subject>Multi-component condensation reaction</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kE9rGzEUxEVJoU7aD5Cbjj1Y7tOf3fWSUwltUgjk0p5MEFrpbSOzK20k2cQ-9pNnjXPu6THDzMD7EXLNYcWB19-2q4JlJYCrWa-ghg9kwVWtWKV4fUEWAAqYAgGfyGXOWwDgXMgF-fcYkE2x0HwI5RmzzzT2lC_FUi0rNm8m83xwKbLZYM7H19hhOMZN97ThS_XkvDni5ANSExwdzRCDGb1D6jD5vSl-j5nusg9_6bgbimc2jlMMGApNaGzxMeTP5GNvhoxf3u8V-fPzx-_be_bwePfr9vsDs1JCYb2Fum1b12LFha3qjotWCWwFRwdd52QNLTQoe-dMXzVCNqdo07UojVtLkFfk63l3SvFlh7no0WeLw2ACxl3WvFGqXot1peYoP0dtijkn7PWU_GjSQXPQJ956q2c2-sT7ZM28587NuYPzD3uPSWfrMVh0PqEt2kX_n_YbWVSJvQ</recordid><startdate>20141216</startdate><enddate>20141216</enddate><creator>Rahmati, Abbas</creator><creator>Ahmadi, Samaneh</creator><creator>Ahmadi-Varzaneh, Mahdi</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20141216</creationdate><title>One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions</title><author>Rahmati, Abbas ; Ahmadi, Samaneh ; Ahmadi-Varzaneh, Mahdi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-fc06999d9e512c56b12942e921ed0bbd360907e3fddaf57237d9e57b9e3ad8303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aldehydes</topic><topic>Ambient temperature</topic><topic>Derivatives</topic><topic>Diazepines</topic><topic>Malonamides</topic><topic>Malononitrile</topic><topic>Multi-component condensation reaction</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rahmati, Abbas</creatorcontrib><creatorcontrib>Ahmadi, Samaneh</creatorcontrib><creatorcontrib>Ahmadi-Varzaneh, Mahdi</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rahmati, Abbas</au><au>Ahmadi, Samaneh</au><au>Ahmadi-Varzaneh, Mahdi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions</atitle><jtitle>Tetrahedron</jtitle><date>2014-12-16</date><risdate>2014</risdate><volume>70</volume><issue>50</issue><spage>9512</spage><epage>9521</epage><pages>9512-9521</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile) in CH2Cl2 at ambient temperature. Synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine proceeded via four- and five-component reactions; while the synthesis of malonamide derivatives was performed using five- and six-component reactions. In addition, a new series of the malonamide derivatives have been prepared using an aldehyde, malononitrile, Meldrum's acid, an isocyanide, and two molecules of 1,4-diamine via a six-component reaction. These procedures provide alternative methods to the synthesis of a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives. [Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2014.10.060</doi><tpages>10</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0040-4020
ispartof Tetrahedron, 2014-12, Vol.70 (50), p.9512-9521
issn 0040-4020
1464-5416
language eng
recordid cdi_proquest_miscellaneous_1744682854
source Access via ScienceDirect (Elsevier)
subjects Aldehydes
Ambient temperature
Derivatives
Diazepines
Malonamides
Malononitrile
Multi-component condensation reaction
Synthesis (chemistry)
Tetrahedrons
title One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T17%3A32%3A54IST&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=One-pot%20synthesis%20of%201,2,4,5-tetrahydro-2,4-dioxobenzo%5Bb%5D%5B1,4%5Ddiazepine%20and%20malonamide%20derivatives%20using%20multi-component%20reactions&rft.jtitle=Tetrahedron&rft.au=Rahmati,%20Abbas&rft.date=2014-12-16&rft.volume=70&rft.issue=50&rft.spage=9512&rft.epage=9521&rft.pages=9512-9521&rft.issn=0040-4020&rft.eissn=1464-5416&rft_id=info:doi/10.1016/j.tet.2014.10.060&rft_dat=%3Cproquest_cross%3E1744682854%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=1744682854&rft_id=info:pmid/&rft_els_id=S0040402014015117&rfr_iscdi=true