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)...
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Veröffentlicht in: | Tetrahedron 2014-12, Vol.70 (50), p.9512-9521 |
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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.
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doi_str_mv | 10.1016/j.tet.2014.10.060 |
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[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.
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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 |
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