Some Quinolines Patterned as “Open Models” of Atabrine

Gilman, Henry; Spatz, Sydney M.

doi:10.1021/ja01232a034

Cited by 18 publications

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“…The neutral alumina (Al 2 O 3 ) used for chromatography was deoxygenated at room temperature under high vacuum for 16 h, deactivated with 5% w/w N 2 −saturated water, and stored under N 2 . Compounds 1 and 2 , Et 3 OBF 4 , and aryllithium reagents − were prepared by literature methods.…”

Section: Methodsmentioning

confidence: 99%

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]

1997

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Fukujiro Fujikawa und Itiro Nakamura : Uber die .antiseptische Wirkung von 3-Oxyorsellinsdureestern und 5-Oxyorsellinsaureestern auf Shoyu. Uber die antiseptische Wirkung der Phenole, Phenol-carbonsauren aus denen die Flechtenstoffe zusammengesetzt sind, sowie deren Ester. (XV. Mitteilung). Wir haben diesmal 12 neue Ester, namlich 3-Oxyorsellinsauremethylester, 5-Oxyorsellinsaure-methylester, 3-Oxyorsellinsaureathylester, 5-Oxyorsellinsaureathylester, 3-Oxyorsellinsaure-n-propylester, 5-Oxyorsellinsaure-n-propylester, 3-Oxyorsellinsaure-isopropylester, 5-Oxyorsellin-saure-isopropylester, 3-Oxyorsellinsaure-n-butylester, 5-Oxyorsellinsaure-n-butylester, 3-Oxy-orsellinsaure-isobutylester und 5-Oxyorsellinsaure-isobutylester, synthetisiert. Dann haben wir die antiseptische Wirkung von 9 dieser Ester mit Ausnahme der 5-Oxyorsel-linsaure-n-propylester, 3-Oxyorsellinsaure-isopropylester und 3-Oxyorsellinsaure-isobutylester 1) Diese Ztschr. 60, 164 [1940].

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Section: Methodsmentioning

confidence: 99%

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]

1997

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“…In earlier investigations in this laboratory (8,9,14,15) For personal use only. ) showed slight activity.…”

Section: Introductionmentioning

confidence: 92%

“…2-Arylpyridincs and aryllithiums give low yields of 2,6-diarylpyridines. From three different 2-arylpyridines three antimalarials modelled after the p l a s n~o~l~i n type have been prepared.In earlier investigations in this laboratory (8,9,14,15) For personal use only. ) showed slight activity.…”

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confidence: 92%

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Studies in the Preparation of Antimalarials From Pyridine

Gilman¹,

Edward²

1953

Can. J. Chem.

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The addition of aryllithium compounds to pyridine followed by air oxidation gives satisfactory yields of several 2-arylpyridines. These are readily oxidized by pcrbenzoic acid to 2-arylpyridine-N-oxides, from which 2-aryl-4-and 6-chloropyridines may be obtained. 2-Arylpyridincs and aryllithiums give low yields of 2,6-diarylpyridines. From three different 2-arylpyridines three antimalarials modelled after the p l a s n~o~l~i n type have been prepared.In earlier investigations in this laboratory (8,9,14,15) For personal use only. ) showed slight activity. Somewhat surprisingly, 2-ptolylpyridine also gave indications of activity. I t inay be significant that the active compounds are vinylogues of a-picoline and a 2-aminop)~idine, in both of which there exists the possibility of a tautolileric shift of hydrogen to the hetero nitrogen atom (19, pp. 32, 91) ; such a possibility has been suggested in explaining the antimalarial activity of atebrin (23) and other compounds (4). The general method of synthesis of these plasmoquin models is illustrated by the example below. The aryllithium was prepared in all cases by direct interaction of the appropriate aryl bromide with lithium. I t has been observed that p-anisyllithium metalates p-bromoanisole so that the reaction of the latter with lithium ordinarily yields a mixture of p-anisyllithium and 2-rnethoxy-5-bromophenyllithium (10). However, if the p-anisyllithium is prepared very rapidly, the extent of metalation is slight and relatively pure p-anisyllithium is obtained. CANADIAA' JOURNAL 01; C H E M I S T R Y . I.OL. 31The addition of an aryllithium to pyridiilegives an N-lithiodihydropyridine (VI), which hitherto has been converted to the desired 2-arylpyridine (VII) by heating above 100" and splitting out lithium hydride (5,25,26,27). Oxidation of the N-lithiodihydro intermediate with dry air gives, particularly in the cases of 2-o-anisyl-and 2-p-anisylpyridine, sig;ificantly improved yields, though in the case of the o-anisyl compound the yield is still low.Since this work was completed, the preparation of 2-phenylpyridine in 60% yield by oxidation with nitrobenzene of 2-phenyl-l,2-dihydropyridine (produced from (VI; R = H) when the reaction mixture is poured into water) has been reported (7).The attempt to prepare 2-phenylpyridine by coupling 2-brornopyridine with phenyllithium gave only a low yield of the desired compound; the isolation of pyridine from the hydrolyzed reaction mixture indicates that a halogennletal interconversion reaction took place, giving bromobenzene and 2-pyridyllithium. A similar reaction with 3-bromopyridine, using n-butyllithium, has been described by Gilman and Spatz (12).The nitration of 2-phenyl-and 2-p-anisylpyridine gave nitro compounds of known orientation (6, 16); however, it was necessary to establish the position of nitration of 2-p-tolylpyridine (VII; R = CH3). This was done by an independent synthesis of the product, 2-(3'-nitro-4'-methylpheny1)-pyridine (VIII; R = CHJ, by the reaction of diazotized 2-nitro-4-aminotolu...

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“…To date, only the bromo-and iodo-pyridines and -quinolines have responded to the X-M inter conversion. Compounds containing a-and -chlorine atoms, recognized for their increased reactivity toward hydrolysis, ammonolysis, and etherification by alkoxides, have not yet been found capable of the X-M interconversion reaction (lb, 13). EXPERIMENTAL S-Pyridyllithium, from 3-bromopyridine.…”

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Pyridyllithium Compounds

Gilman¹,

Spatz²

1951

J. Org. Chem.

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109

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Some Quinolines Patterned as “Open Models” of Atabrine

Abstract: Some Quinolines Patterned as "Open Models" of Atabrine 621 needles were obtained which melted at 220°with sublimation. The yield was 55 mg. corresponding to 96% of the theoretical.

Cited by 18 publications

References 0 publications

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]

Studies in the Preparation of Antimalarials From Pyridine

Pyridyllithium Compounds

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Some Quinolines Patterned as “Open Models” of Atabrine

Abstract: Some Quinolines Patterned as "Open Models" of Atabrine 621 needles were obtained which melted at 220°with sublimation. The yield was 55 mg. corresponding to 96% of the theoretical.

Cited by 18 publications

References 0 publications

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)3Fe(m-C10H10)(CO)2FeC(OC2H5)C6H4CH3-o] and [(CO)3Fe(p-C10H10)(CO)2FeC(OC2H5)C6H4CF3-p]

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)3Fe(m-C10H10)(CO)2FeC(OC2H5)C6H4CH3-o] and [(CO)3Fe(p-C10H10)(CO)2FeC(OC2H5)C6H4CF3-p]

Studies in the Preparation of Antimalarials From Pyridine

Pyridyllithium Compounds

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Product

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Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]

Reactions of m- and p-Divinylbenzene−Diiron Hexacarbonyl with Aryllithium Reagents. Crystal Structures of [(CO)₃Fe(m-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CH₃-o] and [(CO)₃Fe(p-C₁₀H₁₀)(CO)₂FeC(OC₂H₅)C₆H₄CF₃-p]