A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction
Molecules with the quinone structure containing nitrogen constitute one of the most interesting classes of compounds in organic chemistry because of their biological properties and their potential as intermediates in the synthesis of heterocycles. This work describes a clean, efficient and facile on...
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Veröffentlicht in: | Tetrahedron letters 2014-07, Vol.55 (31), p.4373-4377 |
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creator | Fiorot, Rodolfo G. Allochio Filho, João F. Pereira, Thieres M.C. Lacerda, Valdemar dos Santos, Reginaldo B. Romão, Wanderson Greco, Sandro J. |
description | Molecules with the quinone structure containing nitrogen constitute one of the most interesting classes of compounds in organic chemistry because of their biological properties and their potential as intermediates in the synthesis of heterocycles. This work describes a clean, efficient and facile one-pot protocol for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.
A clean, efficient and facile one-pot protocol was developed for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH in CH3CN, at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent. |
doi_str_mv | 10.1016/j.tetlet.2014.06.031 |
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A clean, efficient and facile one-pot protocol was developed for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH in CH3CN, at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2014.06.031</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Amines ; Catalysis ; Catalysts ; Catalytic Mannich reaction ; Cleaning ; Lawsone ; Multicomponent reaction ; Reaction time ; Solvents ; Synthesis (chemistry) ; Tetrahedrons</subject><ispartof>Tetrahedron letters, 2014-07, Vol.55 (31), p.4373-4377</ispartof><rights>2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c475t-aacedd38ac1e79e4a7c08fc9f61a7e5741cbc8dfee47b7918de1d8c40841e2043</citedby><cites>FETCH-LOGICAL-c475t-aacedd38ac1e79e4a7c08fc9f61a7e5741cbc8dfee47b7918de1d8c40841e2043</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403914010107$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids></links><search><creatorcontrib>Fiorot, Rodolfo G.</creatorcontrib><creatorcontrib>Allochio Filho, João F.</creatorcontrib><creatorcontrib>Pereira, Thieres M.C.</creatorcontrib><creatorcontrib>Lacerda, Valdemar</creatorcontrib><creatorcontrib>dos Santos, Reginaldo B.</creatorcontrib><creatorcontrib>Romão, Wanderson</creatorcontrib><creatorcontrib>Greco, Sandro J.</creatorcontrib><title>A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction</title><title>Tetrahedron letters</title><description>Molecules with the quinone structure containing nitrogen constitute one of the most interesting classes of compounds in organic chemistry because of their biological properties and their potential as intermediates in the synthesis of heterocycles. This work describes a clean, efficient and facile one-pot protocol for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.
A clean, efficient and facile one-pot protocol was developed for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH in CH3CN, at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.</description><subject>Amines</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalytic Mannich reaction</subject><subject>Cleaning</subject><subject>Lawsone</subject><subject>Multicomponent reaction</subject><subject>Reaction time</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>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kE1PAyEQhonRxPrxDzxw9LIrdOlCLyaN8Sup8aJnQofZlGYXVqA1_Qv-amnqWQ4zE3jfYeYh5IazmjPe3m3qjLnHXE8ZFzVra9bwEzLhSjZVM1P8lEwYE6wSrJmfk4uUNqycVrEJ-VnQ5IaxR2q8pRD8Dr1Dn-mAeR0s7UKkae_zGpNLNHTU4zc1g_PBm3FdJF_bQ42JWoxuh8URw0B7853KLV3tKZhs-n12QIdtX1IYxvJSfngz3jtY04gGsgv-ipx1pk94_ZcvyefT48fDS7V8f359WCwrEHKWK2MArW2UAY5yjsJIYKqDeddyI3EmBYcVKNshCrmSc64scqtAMCU4TploLsntse8Yy_SYsh5cAux74zFsk-ZSiFY1JRapOEohhpQidnqMbjBxrznTB_R6o4_o9QG9Zq0u6Ivt_mjDssbOYdQJCtQyt4sIWdvg_m_wC6YGlCE</recordid><startdate>20140730</startdate><enddate>20140730</enddate><creator>Fiorot, Rodolfo G.</creator><creator>Allochio Filho, João F.</creator><creator>Pereira, Thieres M.C.</creator><creator>Lacerda, Valdemar</creator><creator>dos Santos, Reginaldo B.</creator><creator>Romão, Wanderson</creator><creator>Greco, Sandro J.</creator><general>Elsevier Ltd</general><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>20140730</creationdate><title>A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction</title><author>Fiorot, Rodolfo G. ; Allochio Filho, João F. ; Pereira, Thieres M.C. ; Lacerda, Valdemar ; dos Santos, Reginaldo B. ; Romão, Wanderson ; Greco, Sandro J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c475t-aacedd38ac1e79e4a7c08fc9f61a7e5741cbc8dfee47b7918de1d8c40841e2043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amines</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalytic Mannich reaction</topic><topic>Cleaning</topic><topic>Lawsone</topic><topic>Multicomponent reaction</topic><topic>Reaction time</topic><topic>Solvents</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fiorot, Rodolfo G.</creatorcontrib><creatorcontrib>Allochio Filho, João F.</creatorcontrib><creatorcontrib>Pereira, Thieres M.C.</creatorcontrib><creatorcontrib>Lacerda, Valdemar</creatorcontrib><creatorcontrib>dos Santos, Reginaldo B.</creatorcontrib><creatorcontrib>Romão, Wanderson</creatorcontrib><creatorcontrib>Greco, Sandro J.</creatorcontrib><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>Fiorot, Rodolfo G.</au><au>Allochio Filho, João F.</au><au>Pereira, Thieres M.C.</au><au>Lacerda, Valdemar</au><au>dos Santos, Reginaldo B.</au><au>Romão, Wanderson</au><au>Greco, Sandro J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction</atitle><jtitle>Tetrahedron letters</jtitle><date>2014-07-30</date><risdate>2014</risdate><volume>55</volume><issue>31</issue><spage>4373</spage><epage>4377</epage><pages>4373-4377</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Molecules with the quinone structure containing nitrogen constitute one of the most interesting classes of compounds in organic chemistry because of their biological properties and their potential as intermediates in the synthesis of heterocycles. This work describes a clean, efficient and facile one-pot protocol for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.
A clean, efficient and facile one-pot protocol was developed for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH in CH3CN, at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2014.06.031</doi><tpages>5</tpages></addata></record> |
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subjects | Amines Catalysis Catalysts Catalytic Mannich reaction Cleaning Lawsone Multicomponent reaction Reaction time Solvents Synthesis (chemistry) Tetrahedrons |
title | A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction |
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