Publication detail

Reduction of 3-Aminoquinoline-2,4(1H,3H)-diones and Deamination of the Reaction Products

Authors: Klásek Antonín | Lyčka Antonín | Rouchal Michal | Rudolf Ondřej | Růžička Aleš

Year: 2014

Type of publication: článek v odborném periodiku

Name of source: Helvetica Chimica Acta

Publisher name: Wiley-VCH

Place: Weinheim

Page from-to: 595-612

Titles:

Language	Name	Abstract	Keywords
cze	Redukce 3-aminochinolin-2,4(1H,3H)-dionů a určení produktů	3-Aminoquinoline-2,4-diony byly stereoselektivně zredukovány pomocí NaBH4 na cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ony. Tyto sloučeniny byly pomocí triphosgenu (=bis(trichloromethyl) karbonát) převedeny na 3,3a-dihydrooxazolo[4,5-c]quinoline-2,4(5H,9bH)-diony. Deaminace pomocí HNO2 zredukovaných produktů poskytovala směs několika sloučenin, z nichž byly izolovány 3-alkyl/aryl-2,3-dihydro-1H-indol-2-ony a jejich 3-hydroxy and 3-nitro deriváty jakožto produkty molekulového přesmyku.
eng	Reduction of 3-Aminoquinoline-2,4(1H,3H)-diones and Deamination of the Reaction Products	3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-c]quinoline-2,4(5H,9bH)-diones. The deamination of the reduction products using HNO2 afforded mixtures of several compounds, from which 3-alkyl/aryl-2,3-dihydro-1H-indol-2-ones and their 3-hydroxy and 3-nitro derivatives were isolated as the products of the molecular rearrangement.	Alcohols; -amino-; Quinoline-2; 4-diones; 3-amino-; Rearrangement reactions; Oxazolo[4; 5-c]quinoline-2; 4(5H; 9bH)-diones; 3; 3a-dihydro-; Nitrous acid

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