Antimalarials. II. 8-Quinolinemethanols

Gillespie, J. S.; Acharya, S. P.; Davis, Richard E.; Barman, Biraj Kumar

doi:10.1021/jm00299a016

Cited by 6 publications

(2 citation statements)

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“…The prepns of 2-bromo-l,4-dimethyl-5-nitroimid-azole2 and its precursors [2-bromo-4(5 )-methyl-5 (4)-nitroimidaz- azole9] were carried out by previously published procedures, as indicated. l,4-Dimethyl-5-nitro-2-piperidinoimidazole (5).-A soln of 11.5 g (0.054 mole) of 2-bromo-1,4-dimethyl-5-nitroimidazole (4) and 37.5 ml (ca. 0.35 mole) of piperidine in 1 1. of abs EtOH was refluxed for 1 hr and the solvent was removed.…”

Section: Methodsmentioning

confidence: 99%

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2-Amino-5-nitroimidazoles

Miller¹,

Bambury²

1971

J. Med. Chem.

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Notes described above for 7a ( = 2, 4) except that the vols of H20 and DMF were increased 2.5-3 times.IV. S,S'-3,8-Diazaundecamethylenebis (dihydrogen phosphorothioate) (8a) was prepared by the procedure used for the prepn of 7a ( = 2,4).V. N,N'-(trans-l, 4-Cyclohexylene )bis(Y'-(czs-l,4-Cyclohexyienedimethylene)bis(S-2-aminoethyl lithium hydrogen phosphorothioate) (13a) was prepd in the manner described for 12a (re = 1). 2,2'-[

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Section: Methodsmentioning

confidence: 99%

“…A sample of 3 was methylated with Me2S04 to give 2-bromo-l,4-dimethyl-5-nitroimidazole2 (4). Reaction of 4 with piperidine in refluxing EtOH proceeded smoothly to give a high yield of l,4-dimethyl-5-nitro-2-piperidinoimidazole (5).…”

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confidence: 99%

2-Amino-5-nitroimidazoles

Miller¹,

Bambury²

1971

J. Med. Chem.

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Quinoline Aldehydes

Greenhill¹

1990

Chemistry of Heterocyclic Compounds: A Series of Monographs

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ChemInform Abstract: MALARIAMITTEL 2. MITT. 8‐CHINOLINMETHYLOLE

Gillespie¹,

Acharya²,

Davis³

et al. 1971

Chemischer Informationsdienst. Organische Chemie

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Durch Kondensation von 4‐ und 5‐Chloranthranilsäure (I) mit Methylvinylketon in Gegenwart von FeCl3 werden die 8‐Chinolincarbonsäuren (II) in 60%iger Ausbeute erhalten, mit Diazomethan in die Methylester (III) übergeführt, mit LiAlH4 zu den 8‐Chinolinmethylolen (IV) reduziert, weiter mit Pyridin‐SO3 in Dimethylsulfoxid zu den Aldehyden (V) oxidiert, mit Dimethylsulfoniummethylid in die Oxirane (VI) und schließlich mit Aminen zu den α‐(Dialkylaminomethyl)‐8‐chinolinmethylolen (VII) kondensiert.

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Antimalarials. II. 8-Quinolinemethanols

Cited by 6 publications

References 1 publication

2-Amino-5-nitroimidazoles

2-Amino-5-nitroimidazoles

Quinoline Aldehydes

ChemInform Abstract: MALARIAMITTEL 2. MITT. 8‐CHINOLINMETHYLOLE

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