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  • This report describes new synthetic approach to symmetrical diamino Tr?ger's base analogues allowing synthesis of 1,7-, and 4,10-diamino derivatives with no additional substituents and 3,9-diamino derivative with methyl groups in the 1,4,7 and 10 positions. The synthesis uses regioselective nitration of the dihalogen or tetrahalogen Tr?ger's bases followed by hydrogenation of the nitro functions accompanied by removal of halogen atoms. Alternatively, chemoselective reduction of nitro groups can be used to obtain the dihalogen diamino Tr?ger's base analogues. The 2,8-diamino derivatives, which are not accessible using this approach, can be prepared by Buchwald-Hartwig amination of the 2,8-dibromo Tr?ger's bases.
  • This report describes new synthetic approach to symmetrical diamino Tr?ger's base analogues allowing synthesis of 1,7-, and 4,10-diamino derivatives with no additional substituents and 3,9-diamino derivative with methyl groups in the 1,4,7 and 10 positions. The synthesis uses regioselective nitration of the dihalogen or tetrahalogen Tr?ger's bases followed by hydrogenation of the nitro functions accompanied by removal of halogen atoms. Alternatively, chemoselective reduction of nitro groups can be used to obtain the dihalogen diamino Tr?ger's base analogues. The 2,8-diamino derivatives, which are not accessible using this approach, can be prepared by Buchwald-Hartwig amination of the 2,8-dibromo Tr?ger's bases. (en)
Title
  • Novel synthesis of symmetrical dinitro and diamino Tr?ger's base analogues
  • Novel synthesis of symmetrical dinitro and diamino Tr?ger's base analogues (en)
skos:prefLabel
  • Novel synthesis of symmetrical dinitro and diamino Tr?ger's base analogues
  • Novel synthesis of symmetrical dinitro and diamino Tr?ger's base analogues (en)
skos:notation
  • RIV/60461373:22310/12:43894882!RIV13-MSM-22310___
http://linked.open...avai/riv/aktivita
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  • S
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  • 36
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  • 154814
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  • RIV/60461373:22310/12:43894882
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  • Chirality; Reduction; Aromatic substitution; Supramolecular building blocks; Tr?ger's bases (en)
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  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [B1616FC17B8F]
http://linked.open...i/riv/nazevZdroje
  • European Journal of Organic Chemistry
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http://linked.open...UplatneniVysledku
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  • Neuveden
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  • Cibulka, Radek
  • Šturala, Jiří
http://linked.open...ain/vavai/riv/wos
  • 000312223500006
issn
  • 1434-193X
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/ejoc.201201188
http://localhost/t...ganizacniJednotka
  • 22310
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