Notiz über synthetische Cyclopeptide mit Dihydrochinolinbausteinen

Gündel, Wolf‐H.; Bohnert, S.

doi:10.1002/jlac.198619860220

Liebigs Ann. Chem.

1986

DOI: 10.1002/jlac.198619860220

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Notiz über synthetische Cyclopeptide mit Dihydrochinolinbausteinen

Wolf‐H. Gündel

S. Bohnert

Abstract: Note on Synthetic Cyclopeptides with Dihydroquinoline Units Quaternary salts of the amides of N‐(3‐quinolylcarbonyl)amino acids 4 cyclise under the influence of base to give fourteen‐membered rings 7.

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Cited by 3 publications

References 12 publications

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Diastereoselektive Ringschlußreaktion zum Pyrrolodiazepino‐chinolin

Gündel

Bohnert

1986

Liebigs Ann. Chem.

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Cyclization to Pyrrolodiazepino‐quinoline, a Diastereoselective Reaction Quaternary salts of N‐(3‐quinolinylcarbonyl)‐L‐prolinamide 5b, c cyclize under the influence of base to pyrrolodiazepino‐quinolines 6b, c with an additional dissymmetric carbon atom. The reaction yields the pure enantiomers 6b, c with high diastereoselectivity. The salt with a sarcosine moiety (5a) forms the racemic diazepino‐quinoline 6a under the same conditions.

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Diastereoselektive Ringschlußreaktion zum Pyrrolodiazepino‐chinolin

Gündel

Bohnert

1986

Liebigs Ann. Chem.

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Cyclisierung von Chinolinium‐Salzen mit peptidartiger Seitenkette

Gündel

Bohnert

1988

Liebigs Ann. Chem.

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Amidcs or diand tripcpridcs. substituted with a 3-quinolinccarbonyl group at thc N terminus have becn prcparcd and quaicrnatcd to 5. These salts dtmcrisc under thc influence of base tu givc rhc oyclopptidelikc substances 6 with twenty-or twentyix-niembcred rings. respectively.Die Anlagerung von Carboxamidgruppen an quartare Pyridin i~m '~~' , aber auch Chinolini~m-Salze~~~), ist als intra-und intermolekulare Reaktion bekannt und erscheint durch die ldee interessant, daD auch das Coenzym NAD durch Peptide auf diese Weise gebunden werden konnte. Diese Additionsreaktion wurde jetzt ausgenutzt, urn cyclohexa-oder cyclooctapeptidartige Verbindungen mit Dihydrochinolinpartialstruktur darzustellen.

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Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

et al. 2008

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The first N1-alkyl-4-amino-1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51% overall yield via the corresponding furo[3,4-b]quinolin-1(3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-didehydropodophyllotoxins.

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Notiz über synthetische Cyclopeptide mit Dihydrochinolinbausteinen

Abstract: Note on Synthetic Cyclopeptides with Dihydroquinoline Units Quaternary salts of the amides of N‐(3‐quinolylcarbonyl)amino acids 4 cyclise under the influence of base to give fourteen‐membered rings 7.

Cited by 3 publications

References 12 publications

Diastereoselektive Ringschlußreaktion zum Pyrrolodiazepino‐chinolin

Diastereoselektive Ringschlußreaktion zum Pyrrolodiazepino‐chinolin

Cyclisierung von Chinolinium‐Salzen mit peptidartiger Seitenkette

Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

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