First ultrasound-mediated one-pot synthesis of N-substituted amides
Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl ca...
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| Veröffentlicht in: | Ultrasonics sonochemistry 2009-08, Vol.16 (6), p.737-742 |
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| container_title | Ultrasonics sonochemistry |
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| creator | Srivastava, Rajendra M. Neves Filho, Ricardo A.W. da Silva, Cecilia A. Bortoluzzi, Adailton J. |
| description | Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl carboxylic acids as well as with aromatic or aliphatic amines. This methodology is expeditious and reliable for preparing secondary carboxamides which in many cases are embedded in the C-5 side-chain of 1,2,4-oxadiazoles (
14,
15, 17–
27). The elemental analyses of new compounds (
19–
27) in conjunction with the spectral data of all synthesized amides gave an idea about their structures, while the crystallographic data of one of the compounds (
26) supplied information concerning the configurational behavior of the amidic part and also the conformational aspect of the entire molecule in the crystalline state. |
| doi_str_mv | 10.1016/j.ultsonch.2009.04.006 |
| format | Article |
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14,
15, 17–
27). The elemental analyses of new compounds (
19–
27) in conjunction with the spectral data of all synthesized amides gave an idea about their structures, while the crystallographic data of one of the compounds (
26) supplied information concerning the configurational behavior of the amidic part and also the conformational aspect of the entire molecule in the crystalline state.</description><identifier>ISSN: 1350-4177</identifier><identifier>EISSN: 1873-2828</identifier><identifier>DOI: 10.1016/j.ultsonch.2009.04.006</identifier><identifier>PMID: 19435673</identifier><language>eng</language><publisher>Kidlington: Elsevier B.V</publisher><subject>1,2,4-Oxadiazoles ; Amides ; Amides - chemical synthesis ; Amides - chemistry ; Carbonates - chemistry ; Chemistry ; Ethyl chloroformate ; Exact sciences and technology ; General and physical chemistry ; Indicators and Reagents - chemistry ; Kinetics ; Nitrogen - chemistry ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics) ; Potassium - chemistry ; Ultrasonic chemistry ; Ultrasonics ; Ultrasound ; X-ray crystallography</subject><ispartof>Ultrasonics sonochemistry, 2009-08, Vol.16 (6), p.737-742</ispartof><rights>2009</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-25ade4c013fbbf1f1a0844c6ae2fbfddd30e466900be5f4a6684fb6c824b716b3</citedby><cites>FETCH-LOGICAL-c396t-25ade4c013fbbf1f1a0844c6ae2fbfddd30e466900be5f4a6684fb6c824b716b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ultsonch.2009.04.006$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27911,27912,45982</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21635400$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19435673$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Srivastava, Rajendra M.</creatorcontrib><creatorcontrib>Neves Filho, Ricardo A.W.</creatorcontrib><creatorcontrib>da Silva, Cecilia A.</creatorcontrib><creatorcontrib>Bortoluzzi, Adailton J.</creatorcontrib><title>First ultrasound-mediated one-pot synthesis of N-substituted amides</title><title>Ultrasonics sonochemistry</title><addtitle>Ultrason Sonochem</addtitle><description>Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl carboxylic acids as well as with aromatic or aliphatic amines. This methodology is expeditious and reliable for preparing secondary carboxamides which in many cases are embedded in the C-5 side-chain of 1,2,4-oxadiazoles (
14,
15, 17–
27). The elemental analyses of new compounds (
19–
27) in conjunction with the spectral data of all synthesized amides gave an idea about their structures, while the crystallographic data of one of the compounds (
26) supplied information concerning the configurational behavior of the amidic part and also the conformational aspect of the entire molecule in the crystalline state.</description><subject>1,2,4-Oxadiazoles</subject><subject>Amides</subject><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Carbonates - chemistry</subject><subject>Chemistry</subject><subject>Ethyl chloroformate</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Indicators and Reagents - chemistry</subject><subject>Kinetics</subject><subject>Nitrogen - chemistry</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Potassium - chemistry</subject><subject>Ultrasonic chemistry</subject><subject>Ultrasonics</subject><subject>Ultrasound</subject><subject>X-ray crystallography</subject><issn>1350-4177</issn><issn>1873-2828</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhq2Kqh8Lf6HKBW4J49hxkhtoRaFSRS9wtvwxVr3KJovHQeq_r1e7wJHTzOF55-Nh7I5Dw4Grj7tmnTIts3tuWoCxAdkAqAt2w4de1O3QDm9KLzqoJe_7a3ZLtAMAMbZwxa75KEWnenHDtvcxUa7KsGRoWWdf79FHk9FXy4z1YckVvcz5GSlStYTqe02rpRzzekTMPnqkt-wymInw3blu2M_7Lz-23-rHp68P28-PtROjynXbGY_SARfB2sADNzBI6ZTBNtjgvReAUqkRwGIXpFFqkMEqN7TS9lxZsWEfTnMPafm1ImW9j-RwmsyMy0q6PARSjLyA6gS6tBAlDPqQ4t6kF81BH_Xpnf6jTx_1aZC66CvBu_OG1RYP_2JnXwV4fwYMOTOFZGYX6S_XciU6WTRv2KcTh8XH74hJk4s4u-I2ocvaL_F_t7wCvluS5A</recordid><startdate>20090801</startdate><enddate>20090801</enddate><creator>Srivastava, Rajendra M.</creator><creator>Neves Filho, Ricardo A.W.</creator><creator>da Silva, Cecilia A.</creator><creator>Bortoluzzi, Adailton J.</creator><general>Elsevier B.V</general><general>Elsevier</general><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>20090801</creationdate><title>First ultrasound-mediated one-pot synthesis of N-substituted amides</title><author>Srivastava, Rajendra M. ; Neves Filho, Ricardo A.W. ; da Silva, Cecilia A. ; Bortoluzzi, Adailton J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-25ade4c013fbbf1f1a0844c6ae2fbfddd30e466900be5f4a6684fb6c824b716b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>1,2,4-Oxadiazoles</topic><topic>Amides</topic><topic>Amides - chemical synthesis</topic><topic>Amides - chemistry</topic><topic>Carbonates - chemistry</topic><topic>Chemistry</topic><topic>Ethyl chloroformate</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Indicators and Reagents - chemistry</topic><topic>Kinetics</topic><topic>Nitrogen - chemistry</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>Potassium - chemistry</topic><topic>Ultrasonic chemistry</topic><topic>Ultrasonics</topic><topic>Ultrasound</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Srivastava, Rajendra M.</creatorcontrib><creatorcontrib>Neves Filho, Ricardo A.W.</creatorcontrib><creatorcontrib>da Silva, Cecilia A.</creatorcontrib><creatorcontrib>Bortoluzzi, Adailton J.</creatorcontrib><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>Ultrasonics sonochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Srivastava, Rajendra M.</au><au>Neves Filho, Ricardo A.W.</au><au>da Silva, Cecilia A.</au><au>Bortoluzzi, Adailton J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>First ultrasound-mediated one-pot synthesis of N-substituted amides</atitle><jtitle>Ultrasonics sonochemistry</jtitle><addtitle>Ultrason Sonochem</addtitle><date>2009-08-01</date><risdate>2009</risdate><volume>16</volume><issue>6</issue><spage>737</spage><epage>742</epage><pages>737-742</pages><issn>1350-4177</issn><eissn>1873-2828</eissn><abstract>Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl carboxylic acids as well as with aromatic or aliphatic amines. This methodology is expeditious and reliable for preparing secondary carboxamides which in many cases are embedded in the C-5 side-chain of 1,2,4-oxadiazoles (
14,
15, 17–
27). The elemental analyses of new compounds (
19–
27) in conjunction with the spectral data of all synthesized amides gave an idea about their structures, while the crystallographic data of one of the compounds (
26) supplied information concerning the configurational behavior of the amidic part and also the conformational aspect of the entire molecule in the crystalline state.</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><pmid>19435673</pmid><doi>10.1016/j.ultsonch.2009.04.006</doi><tpages>6</tpages></addata></record> |
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| ispartof | Ultrasonics sonochemistry, 2009-08, Vol.16 (6), p.737-742 |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 1,2,4-Oxadiazoles Amides Amides - chemical synthesis Amides - chemistry Carbonates - chemistry Chemistry Ethyl chloroformate Exact sciences and technology General and physical chemistry Indicators and Reagents - chemistry Kinetics Nitrogen - chemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Potassium - chemistry Ultrasonic chemistry Ultrasonics Ultrasound X-ray crystallography |
| title | First ultrasound-mediated one-pot synthesis of N-substituted amides |
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