IndiumV3, Main, Repository, bibRecord, 001980

Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines

Identifieur interne : 001980 ( Main/Repository ); précédent : 001979; suivant : 001981

Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines

Auteurs : RBID : Pascal:12-0441856

Descripteurs français

Pascal (Inist)
- Indium, Hétérocycle azote, Imine, Nitramine, Brome composé organique, Brome Composé organique, Propane(2-nitro), Sélectivité, Composé chiral, Oside, Stéréosélectivité, Synthèse chimique, Addition nucléophile, Amine, Aldolisation, Ethane(nitro), Réaction de Henry, Réaction Henry.

English descriptors

KwdEn :
- Aldol condensation, Amine, Bromine Organic compounds, Chemical synthesis, Chiral compound, Henry reaction, Imine, Indium, Nitramine, Nitrogen heterocycle, Nucleophilic addition, Organic bromine compounds, Oside, Selectivity, Stereoselectivity.

Abstract

A new method has been developed to obtain 2-nitroamines by an indium-promoted reaction of bromonitromethane with a variety of imines. On the strength of these results, the reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroamines. Moreover, the indium-mediated reaction of 1-bromo-1-nitroethane and imines afforded 1-methyl-2-nitroamines with remarkably high anti selectivity. The use of chiral sugar-derived imines furnished the corresponding 2-nitroamines with excellent stereoselectivity.

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Pascal:12-0441856

Le document en format XML

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<author><name sortKey="Soengas, Raquel G" uniqKey="Soengas R">Raquel G. Soengas</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Departament of Chemistry & QOPNA, University of Aveiro</s1>
<s2>3810-193 Aveiro</s2>
<s3>PRT</s3>
<sZ>1 aut.</sZ>
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<country>Portugal</country>
<wicri:noRegion>3810-193 Aveiro</wicri:noRegion>
</affiliation>
<affiliation wicri:level="2"><inist:fA14 i1="02"><s1>Centro Singular de Investigación en Quimica Biológica y Materiales Moleculares, Campus Vida, Universidad de Santiago de Compostela, Jenaro de la Fuente s/n</s1>
<s2>15782, Santiago de Compostela</s2>
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<country>Espagne</country>
<placeName><region nuts="2" type="communauté">Galice</region>
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<author><name sortKey="Silva, Sandrina" uniqKey="Silva S">Sandrina Silva</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Departament of Chemistry & QOPNA, University of Aveiro</s1>
<s2>3810-193 Aveiro</s2>
<s3>PRT</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
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<country>Portugal</country>
<wicri:noRegion>3810-193 Aveiro</wicri:noRegion>
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</author>
<author><name sortKey="Estevez, Amalia M" uniqKey="Estevez A">Amalia M. Estevez</name>
<affiliation wicri:level="2"><inist:fA14 i1="02"><s1>Centro Singular de Investigación en Quimica Biológica y Materiales Moleculares, Campus Vida, Universidad de Santiago de Compostela, Jenaro de la Fuente s/n</s1>
<s2>15782, Santiago de Compostela</s2>
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<author><name sortKey="Estevez, Juan C" uniqKey="Estevez J">Juan C. Estevez</name>
<affiliation wicri:level="2"><inist:fA14 i1="02"><s1>Centro Singular de Investigación en Quimica Biológica y Materiales Moleculares, Campus Vida, Universidad de Santiago de Compostela, Jenaro de la Fuente s/n</s1>
<s2>15782, Santiago de Compostela</s2>
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</placeName>
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<author><name sortKey="Estevez, Ram N J" uniqKey="Estevez R">Ram N J. Estevez</name>
<affiliation wicri:level="2"><inist:fA14 i1="02"><s1>Centro Singular de Investigación en Quimica Biológica y Materiales Moleculares, Campus Vida, Universidad de Santiago de Compostela, Jenaro de la Fuente s/n</s1>
<s2>15782, Santiago de Compostela</s2>
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<placeName><region nuts="2" type="communauté">Galice</region>
</placeName>
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</author>
<author><name sortKey="Rodriguez Solla, Humberto" uniqKey="Rodriguez Solla H">Humberto Rodriguez-Solla</name>
<affiliation wicri:level="2"><inist:fA14 i1="03"><s1>Departamento de Quimica Organica e Inorgánica, Facultad de Quimica, Universidad de Oviedo, Julián Claveria 8</s1>
<s2>33071 Oviedo</s2>
<s3>ESP</s3>
<sZ>6 aut.</sZ>
</inist:fA14>
<country>Espagne</country>
<placeName><region nuts="2" type="communauté">Principauté des Asturies</region>
</placeName>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="inist">12-0441856</idno>
<date when="2012">2012</date>
<idno type="stanalyst">PASCAL 12-0441856 INIST</idno>
<idno type="RBID">Pascal:12-0441856</idno>
<idno type="wicri:Area/Main/Corpus">001571</idno>
<idno type="wicri:Area/Main/Repository">001980</idno>
</publicationStmt>
<seriesStmt><idno type="ISSN">1434-193X</idno>
<title level="j" type="abbreviated">Eur. j. org. chem. : (Print)</title>
<title level="j" type="main">European journal of organic chemistry : (Print)</title>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldol condensation</term>
<term>Amine</term>
<term>Bromine Organic compounds</term>
<term>Chemical synthesis</term>
<term>Chiral compound</term>
<term>Henry reaction</term>
<term>Imine</term>
<term>Indium</term>
<term>Nitramine</term>
<term>Nitrogen heterocycle</term>
<term>Nucleophilic addition</term>
<term>Organic bromine compounds</term>
<term>Oside</term>
<term>Selectivity</term>
<term>Stereoselectivity</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Indium</term>
<term>Hétérocycle azote</term>
<term>Imine</term>
<term>Nitramine</term>
<term>Brome composé organique</term>
<term>Brome Composé organique</term>
<term>Propane(2-nitro)</term>
<term>Sélectivité</term>
<term>Composé chiral</term>
<term>Oside</term>
<term>Stéréosélectivité</term>
<term>Synthèse chimique</term>
<term>Addition nucléophile</term>
<term>Amine</term>
<term>Aldolisation</term>
<term>Ethane(nitro)</term>
<term>Réaction de Henry</term>
<term>Réaction Henry</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A new method has been developed to obtain 2-nitroamines by an indium-promoted reaction of bromonitromethane with a variety of imines. On the strength of these results, the reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroamines. Moreover, the indium-mediated reaction of 1-bromo-1-nitroethane and imines afforded 1-methyl-2-nitroamines with remarkably high anti selectivity. The use of chiral sugar-derived imines furnished the corresponding 2-nitroamines with excellent stereoselectivity.</div>
</front>
</TEI>
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</fA01>
<fA03 i2="1"><s0>Eur. j. org. chem. : (Print)</s0>
</fA03>
<fA06><s2>23</s2>
</fA06>
<fA08 i1="01" i2="1" l="ENG"><s1>Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines</s1>
</fA08>
<fA11 i1="01" i2="1"><s1>SOENGAS (Raquel G.)</s1>
</fA11>
<fA11 i1="02" i2="1"><s1>SILVA (Sandrina)</s1>
</fA11>
<fA11 i1="03" i2="1"><s1>ESTEVEZ (Amalia M.)</s1>
</fA11>
<fA11 i1="04" i2="1"><s1>ESTEVEZ (Juan C.)</s1>
</fA11>
<fA11 i1="05" i2="1"><s1>ESTEVEZ (Ramón J.)</s1>
</fA11>
<fA11 i1="06" i2="1"><s1>RODRIGUEZ-SOLLA (Humberto)</s1>
</fA11>
<fA14 i1="01"><s1>Departament of Chemistry & QOPNA, University of Aveiro</s1>
<s2>3810-193 Aveiro</s2>
<s3>PRT</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
</fA14>
<fA14 i1="02"><s1>Centro Singular de Investigación en Quimica Biológica y Materiales Moleculares, Campus Vida, Universidad de Santiago de Compostela, Jenaro de la Fuente s/n</s1>
<s2>15782, Santiago de Compostela</s2>
<s3>ESP</s3>
<sZ>1 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
</fA14>
<fA14 i1="03"><s1>Departamento de Quimica Organica e Inorgánica, Facultad de Quimica, Universidad de Oviedo, Julián Claveria 8</s1>
<s2>33071 Oviedo</s2>
<s3>ESP</s3>
<sZ>6 aut.</sZ>
</fA14>
<fA20><s1>4339-4346</s1>
</fA20>
<fA21><s1>2012</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>26693</s2>
<s5>354000508143350090</s5>
</fA43>
<fA44><s0>0000</s0>
<s1>© 2012 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA45><s0>30 ref.</s0>
</fA45>
<fA47 i1="01" i2="1"><s0>12-0441856</s0>
</fA47>
<fA60><s1>P</s1>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>European journal of organic chemistry : (Print)</s0>
</fA64>
<fA66 i1="01"><s0>DEU</s0>
</fA66>
<fC01 i1="01" l="ENG"><s0>A new method has been developed to obtain 2-nitroamines by an indium-promoted reaction of bromonitromethane with a variety of imines. On the strength of these results, the reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroamines. Moreover, the indium-mediated reaction of 1-bromo-1-nitroethane and imines afforded 1-methyl-2-nitroamines with remarkably high anti selectivity. The use of chiral sugar-derived imines furnished the corresponding 2-nitroamines with excellent stereoselectivity.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>001C03C06</s0>
</fC02>
<fC02 i1="02" i2="X"><s0>001C03C07A</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Indium</s0>
<s2>NC</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Indium</s0>
<s2>NC</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Indio</s0>
<s2>NC</s2>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Hétérocycle azote</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Imine</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Imine</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Imina</s0>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Nitramine</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Nitramine</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Nitramina</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="3" l="FRE"><s0>Brome composé organique</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="3" l="ENG"><s0>Organic bromine compounds</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Brome Composé organique</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Bromine Organic compounds</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Bromo Compuesto orgánico</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Propane(2-nitro)</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Sélectivité</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Selectivity</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Selectividad</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Composé chiral</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Chiral compound</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Compuesto quiral</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Oside</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Oside</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Osido</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Stéréosélectivité</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Stereoselectivity</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Estereoselectividad</s0>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>12</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Addition nucléophile</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Nucleophilic addition</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Adición nucleófila</s0>
<s5>13</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Amine</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Amine</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Amina</s0>
<s5>14</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Aldolisation</s0>
<s5>41</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Aldol condensation</s0>
<s5>41</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Aldolización</s0>
<s5>41</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Ethane(nitro)</s0>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Réaction de Henry</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Henry reaction</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>Réaction Henry</s0>
<s4>CD</s4>
<s5>97</s5>
</fC03>
<fC03 i1="18" i2="X" l="ENG"><s0>Henry reaction</s0>
<s4>CD</s4>
<s5>97</s5>
</fC03>
<fN21><s1>345</s1>
</fN21>
<fN44 i1="01"><s1>OTO</s1>
</fN44>
<fN82><s1>OTO</s1>
</fN82>
</pA>
</standard>
</inist>
</record>

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Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines

Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines

Descripteurs français

English descriptors

Abstract

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