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1998 (2)
1997 (1)
1Author    H. Möhrle, J. MehrensRequires cookie*
 Title    Nachbargruppenbeteiligung bei der Dehydrierung cyclischer Amine vom Typ o-substituierter Anilinderivate Neighbourgroup Participation with the Dehydrogenation of Cyclic Amines of the o-Substituted Aniline Type  
 Abstract    The 2-Aminobenzylalcohols la -c produced with mercury-edta dehydrogenation the lac­ tams 6a -c; the pipecoline 2b yielded the benzoxazine 3b indicating the participation of the nucleophilic hydroxymethyl group. The 2-aminobenzaldehydes showed a different behaviour in dependence on the ring size of the amine part: 7a, b led -via intermediate reaction of the hemiaminal 9 with the electrophilic formyl function -to the lactams 1 la, b, while 7c gave rise to the aminoaldehyde 12 as major product and similarly the pipecoline 15 to the aminoketone 16. From 2'-(4-morpholinyl)-acetophenone (22) were received the lactam 31 and the aminoethanol 32, both by a twofold dehydrogenation. 
  Reference    Z. Naturforsch. 53b, 1369—1378 (1998); eingegangen am 21. Juli 1998 
  Published    1998 
  Keywords    Lactam, Hemiaminal, Aminoaldehyde, Ring-Chain Isomerism, Aminoalkylation 
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 TEI-XML for    default:Reihe_B/53/ZNB-1998-53b-1369.pdf 
 Identifier    ZNB-1998-53b-1369 
 Volume    53 
2Author    H. Möhrle, J. MehrensRequires cookie*
 Title    Reaktivität nitrophenylsubstituierter cyclischer Amine bei Dehydrierungen The Reactivity of Nitrophenyl Substituted Cyclic Amines with Dehydrogenations  
 Abstract    Piperidine and perhydroazepine bearing a 1 -(4-nitrophenyl) substituent were inert to mercury-edta, while the a-pipecoline derivative gave an aminoketone with cleavage of the heterocycle. However the corresponding (2-nitrophenyl) compounds reacted to give respectively a piperidin-2-one, an aminopentanal and an aminohexanone. By an additional substituent in 2'-position the p-nitro compounds underwent dehydrogenation too. With a methyl group resulted a pattern analogous to o-nitro products. A neighbouring hydroxymethyl function enhanced the reaction with formation of benzoxazines and if possible their further oxidized derivatives, the hydroxylactams. 
  Reference    (Z. Naturforsch. 53b, 37 [1998]; eingegangen am 8. Oktober 1997) 
  Published    1998 
  Keywords    Lactam, Iminium Salt, Aminoketone, N, 0-Acetal, Neighbour Group 
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 TEI-XML for    default:Reihe_B/53/ZNB-1998-53b-0037.pdf 
 Identifier    ZNB-1998-53b-0037 
 Volume    53 
3Author    H. Möhrle, M. JeandréeRequires cookie*
 Title    ,3-Dioxolane von N-substituierten 4-Piperidonen als Dehydrierungssubstrat 1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations  
 Abstract    The applicability of ketals was examined for masking the carbonyl group in N-tertiary 4-piperidones during the dehydrogenation using mercury-edta. Various 1,3-dioxolanes showed a different behaviour in dependence on the N-substituent. With simple aliphatic moieties mainly dehydrogenated but hydrolyzed products were received. These enaminones were also available from the dehydrogenations of the corresponding 4-piperidones. Similar applied to para-acyl-aromatic substituted derivatives but with less yields. Aromatic substituents bearing a neighbour group on ortho-position with participation gave rise to different oxidation products partially with preservation of the ketal structure. 
  Reference    (Z. Naturforsch. 52b, 72—78 [1997]; eingegangen am 23. August 1996) 
  Published    1997 
  Keywords    Ketals, Enaminones, N, 0-A cetals, Lactams, Dehydrogenation with Hg-EDTA Complex 
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 TEI-XML for    default:Reihe_B/52/ZNB-1997-52b-0072.pdf 
 Identifier    ZNB-1997-52b-0072 
 Volume    52