1947
DOI: 10.1021/ja01196a015
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1-Alkyl-1,2,3,4-tetrahydroquinoxalines1

Abstract: The intense, wartime search for new chemical series which might show antimalarial activity has

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Cited by 41 publications
(12 citation statements)
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“…1-Benzolsulfo-bzw. 1-Toluolsulfo-Derivate waren aber, wie bereits bekannt [5], ohne Schwierigkeiten darstellbar. Die Umsetzung der Tetrahydrochinoxaline rnit Butylisocyanat fuhrt zu schon kristallisierten 1,4-Bis-butylcarbamaten (LXX, LXXIV).…”
Section: R2unclassified
See 1 more Smart Citation
“…1-Benzolsulfo-bzw. 1-Toluolsulfo-Derivate waren aber, wie bereits bekannt [5], ohne Schwierigkeiten darstellbar. Die Umsetzung der Tetrahydrochinoxaline rnit Butylisocyanat fuhrt zu schon kristallisierten 1,4-Bis-butylcarbamaten (LXX, LXXIV).…”
Section: R2unclassified
“…3-methylierte Chinoxalone wurden am N-1 mit Hilfe von Natriumathylat (XLI, XLV, XLVIII, XLIX, LII, Tab. 3 ) bzw 5). Durch Quartarisierung wurden schon kristallisierte Substanzen rnit charakteristischen Schmelzpunktcn erhalten.…”
unclassified
“…Solvent was removed in roto‐evaporator and the dark brown sticky solid obtained was passed over silica gel column to remove base impurities (Eluent: 70% ethyl acetate in hexane). 6‐Methoxyquinoxaline was obtained as white solid in excellent yield, 13.6 g (85%), mp 58–60°C (Lit mp 60°C [18]).…”
Section: Methodsmentioning
confidence: 99%
“…Cavagnol developed a route for the preparation 1-alkyl derivatives by low temperature acylation with benzenesulfonyl chloride to give the phenylsulfonyl-1,2,3,4tetrahydro-1-quinoxaline, alkylating the monophenylsulfonyl derivative to l-alkyl-4-phenylsulfonyl-l,2,3,4-tetrahydroquinoxaline followed by hydrolysis which yielded 1-alkyl-1,2,3,4-tetrahydroquinoxaline. 14 Later mono and di-substituted alkyl and aryl quinoxalines were rapidly reduced in high yield to their respective 1,2,3,4-tetrahydro-derivatives by borane in THF solution. 15 However, all these methods proceeded with moderate to good yields but required substantial purification procedures and extended reaction times.…”
mentioning
confidence: 99%