A Study of Plasmochin and the Occurrence of Rearrangements in the Preparation of Certain Plasmochin Analogs<sup>1</sup>

Elderfield, Robert C.; Craig, Lyman C.; Lauer, Walter M.; Arnold, Richard T.; Gensler, Walter J.; Head, James D.; Bembry, Thomas H.; Mighton, Harold R.; Tinker, John F.; Galbreath, Jean; Holley, Ann D.; Goldman, Leon; Maynard, John T.; Picus, Norman

doi:10.1021/ja01212a039

Cited by 18 publications

(9 citation statements)

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“…The literature describes various synthetic methods for the preparation of β-aminoalcohols, including the substitution reaction of primary and secondary amines with alkylene chlorohydrins [19][20] ; the reduction of α-hydroxyamides 21 and the opening of 1,2-epoxyalkanes by primary and secondary amines 22 . This last method was chosen because of its simplicity and the availability of starting materials.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Moreira¹,

Piló‐Veloso²,

Nelson³

2000

Quím. Nova

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Moreira¹,

Piló‐Veloso²,

Nelson³

2000

Quím. Nova

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“…The chemical purity of newly synthesized 8-aminoquinolines has been a matter of concern ever since it was found that pamaquine was a mixture of structural isomers (23). In keeping with this concern, each derivative evaluated for toxicity and curative activity during the 1946 to 1952 period was checked for homogeneity via countercurrent distribution (20) The quinine and chloroquine used as companion blood schizonticides in these evaluations were provided, respectively, by Merck & Co., Inc., Rahway, N.J., and the Sterling-Winthrop Research Institute.…”

Section: Methodsmentioning

confidence: 99%

“…The proportions of compounds with such activity in the 2,6-, 4,6-, and 5,6-substituted groups were 23,22, and 16% of the respective totals. These proportions compared with 33, 57, and 67% of all agents with substituents at positions 2,4,6, 2,5,6, and 4,5,6.…”

Section: Generalmentioning

confidence: 96%

Relationships between chemical structures of 8-aminoquinolines and their capacities for radical cure of infections with Plasmodium cynomolgi in rhesus monkeys

Schmidt¹

1983

Antimicrob Agents Chemother

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“…The conversion of 1,2-halohydrin to oxide in the presence of a strong base is rapid and almost quantitative (31, p. 8) but there does not appear to be any definite evidence for formation of oxide in the presence of a weak base such as ammonia, other than the kinetic data of Smith and Nilsson (23). On the other hand Elderfield et al (8) and Petrov and Lagucheva (18) have published data which indicate that amination of 1-chloropentanol-2 with diethylamine or ethylene chlorohydrin with 2,s-dichloroaniline does not proceed via an intermediate oxide stage. Therefore, although oxide can intervene (31), this is not always the case and proof must be sought in each instance.…”

Section: And Discussionmentioning

confidence: 99%

“…Prolonging the time of heating has no significant effect on the yield of amines (runs 2 and 4). Use of only a fivefold excess of ammonia, however, causes a marked drop in the yield of primary amine and a corresponding increase in yield of secondary amines (runs [5][6][7][8] the results of runs 9 to 14 a t room temperature with runs 1 to 8 a t 100'. I t is evident that ammonolysis is much slower a t room temperature, as would be expected.…”

Section: And Discussionmentioning

confidence: 99%

AMMONOLYSIS OF 1,2-EPOXYCYCLOHEXANE AND TRANS-2-BROMOCYCLOHEXANOL

Hawkins¹,

Bannard²

1958

Can. J. Chem.

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Optimum conditions for the preparation of trans-2-aminocyclohexanol by ammonolysis of l,2-epoxycyclohexane or trans-2-bromocyclohexanol are realized by use of a 20-fold excess of aqueous aIcoholic ammonia a t 100'. Under these conditions formation of secondary amines .is minimized. Lower ammonia-reactant ratios, or the use of absolute methanolic atnmonla or aqueous ammonla, lead to lower yields of primary amine and higher yields of secondary amines. 1,2-Epoxycyclohesane has been isolated from the interaction of t m n s -2-bromocyclohexanol with aqueous ammonia. The oside reacts more rapidly with aqueous alcoholic ammonia than the bromohydrin and the rate of conversion of the latter to amine is thus controlled by the rate of conversion of bromohydrin to oxide. INTRODUCTIONWinstein and Henderson (31) have emphasized that reactions involving trans-1,2-halohydrins under basic conditions can proceed via the corresponding oxide as intermediate. If such is the case, approximately equal yields of primary amine should be obtainable from either reactant, and the preferred starting material for preparation of 1,2-aminocyclanols would be the halohydrin rather than the oxide, a synthetic step thereby being eliminated. For the synthesis of a 1,2-aminocyclanol, practical considerations demand that attention be given to the possible intervention of side reactions. Mousseron and Granger (16), for example, fouild in a number of instances that ammonolysis of alicyclic epoxides or 1,2-chlorohydrins led to formation of considerable quantities of secondary amines together with the desired primary amine. Bruilel (4) prepared trans-2-aminocyclohexanol by heating 1,2-epoxycyclohexane with a sixfold excess of aqueous ethanolic ammonia a t 110-115". When a twofold excess of ammonia was used, however, the main products were two diastereoisomeric bis-2-hydroxycyclohexylamii~es (I) of m.p. 114" and 153", subseque~ltly shown by i\~Iousseron and Granger (16) to be dl and meso forms respectively.Godchot and Mousseron (9), however, studying the same reaction, obtained cyclohexadiene a s by-product. Osterberg and Kendall (17) obtained a 61% yield of trans-2-aminocyclohexanol by heating trans-2-chlorocyclohexanol a t 100" with an unspecified excess of aqueous alcoholic ammonia, and reported that omission of the alcohol resulted in formation of secondary and tertiary amines as the main products. They failed, however, to characterize these substances. Wilson and Read (32) studied the same reaction a t room temperature, and did not note formation of by-products. Our purpose was t o determine whether the halohydrin is the preferred starting material and to establish experinlental conditions leading to maximum yield of primary amine, since we required lilfa?zz~script receioed J u I y 15, 1967.

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A Study of Plasmochin and the Occurrence of Rearrangements in the Preparation of Certain Plasmochin Analogs¹

Cited by 18 publications

References 0 publications

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Relationships between chemical structures of 8-aminoquinolines and their capacities for radical cure of infections with Plasmodium cynomolgi in rhesus monkeys

AMMONOLYSIS OF 1,2-EPOXYCYCLOHEXANE AND TRANS-2-BROMOCYCLOHEXANOL

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A Study of Plasmochin and the Occurrence of Rearrangements in the Preparation of Certain Plasmochin Analogs1

Cited by 18 publications

References 0 publications

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Relationships between chemical structures of 8-aminoquinolines and their capacities for radical cure of infections with Plasmodium cynomolgi in rhesus monkeys

AMMONOLYSIS OF 1,2-EPOXYCYCLOHEXANE AND TRANS-2-BROMOCYCLOHEXANOL

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A Study of Plasmochin and the Occurrence of Rearrangements in the Preparation of Certain Plasmochin Analogs¹