A STUDY OF THE ALKYLATION OF HYDRATROPONITRILE WITH BUTYL HALIDES<sup>1</sup>

GOERNER, GORDON L.; WORKMAN, WESLEY R.

doi:10.1021/jo01366a007

Cited by 3 publications

(1 citation statement)

References 8 publications

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“…IV Although Reissert and Goll7 had reported that the reaction of 4-nitro-2-aminodiphenylamine with diethyl oxalate produced some benzimidazole ester in addition to the quinoxaline, all efforts to isolate ethyl 2-benzimidazolecarboxylate from the reaction mixture of o-phenylenediamine with diethyl oxalate were unavailing; only 2, (IV) was obtained. Since acid catalysts might promote the ring closure, these were examined briefly.…”

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confidence: 99%

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Campaigne¹,

Verth²

1958

J. Org. Chem.

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confidence: 99%

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Campaigne¹,

Verth²

1958

J. Org. Chem.

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Addition and Substitution Reactions of Nitrile‐Stabilized Carbanions

1984

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The utilization of carbanions stabilized by various electron‐withdrawing groups to effect carboncarbon bond formation occupies a central position in organic synthesis. This chapter focuses on the reactions of nitrile‐stabilized carbanions with an array of carbon electrophiles and updates another chapter along these lines in this series. Subsequent review articles have dealt with various aspects of the chemistry of nitrile‐stabilized carbanions. In this review, the reactions of nitrile‐stabilized anions are grouped according to the nature of the substituents attached to the carbanion center bearing the nitrile group. These substituents include alkyl, alkenyl, alkynyl, and aryl groups as well as various α‐oriented halogen‐, oxygen‐, nitrogen‐, sulfur‐, and selenium‐containing groups. Notably absent from this survey are the carbanions derived from active methylene compounds bearing two electron‐withdrawing groups such as cyanoacetate esters, malononitriles, α‐sulfonylnitriles, and α‐phosphorylnitriles. Also absent are those carbanions such as Reissert compounds, which are the subject of comprehensive reviews. The chapter is arbitrarily subdivided into six sections: (1) reactions of alkyl‐, aryl‐, and heteroaryl‐substituted nitriles; (2) reactions of α,β‐ and β,γ‐unsaturated nitriles as well as tolunitriles; (3) reactions of cyanohydrins and their hydroxyl‐protected derivatives; (4) reactions of nitriles bearing α‐sulfur and α‐selenium substituents; (5) reactions of α‐(dialkylamino)nitriles; and (6) reactions of α‐halonitriles. Within each of these sections, the reactions are further subdivided according to the nature of the electrophile: (1) alkylation reactions employing alkyl halides, alkyl sulfonates, dialkyl sulfates, and epoxides; (2) arylation reactions involving the substitution of hydrogen, halogen, nitro, or alkoxy groups on aryl or heteroaryl substrates; (3) acylation reactions employing carboxylic esters, anhydrides, acid chlorides, dialkyl carbonates, and nitriles; (4) addition reactions involving aldehydes, ketones, imines, alkenes, and alkynes; and (5) Michael‐type addition reactions to unsaturated aldehydes, ketones, imines, sulfoxides, sulfones, and nitro compounds. Finally, a section involving cyclization reactions is included for each of the six groups of nitrile‐stabilized anions.

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Derivatives of Acetamide and Benzamide as Hypnotics

Mv¹,

Pg²,

Pa³

et al. 1957

Journal of Pharmacy and Pharmacology

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IT has been known since 19101 that certain dialkyl-arylacetamides possess sedative, hypnotic and antipyretic properties, and Lumibre and Perrin2 later described the hypnotic activity of phenylacetamides in dogs. Trialkylacetamides have been reported to possess spasmolytic3 and hypnotic4 properties, but none of the compounds described appears to have found its way into clinical use.Our interest in 3-methylpentynol, and in hypnotics in general, led us to reinvestigate and extend earlier work in this connection, in the hope of discovering a compound with hypnotic properties intermediate between those of methylpentynol and the barbiturates, but without the disadvantages of the latter.Although a number of active compounds were found, none was sufficiently outstanding to justify its introduction to clinical use. Nevertheless, in addition to the preparation of a number of new compounds, we have attempted a correlation of their hypnotic activity and chemical constitution within the group of acetamide derivatives.Benzamide5 has also been reported to possess hypnotic properties and a number of derivatives have been examined, but without discovering any which was of practical interest. NARCOTIC EFFECTThe criterion of narcotic activity adopted was the abolition of the righting reflex in mice. Screening tests were carried out at four geometric dose levels, 1-14, 0.77, 0.52 and 0.35 g./kg. on groups of five female mice (Schofield strain), with methylpentynol as the reference compound in all cases, and observations were made at half an hour, 1 hour, and then hourly intervals up to 6 hours after oral administration of the appropriate dose in suspension in 5 per cent acacia solution. The doses chosen were such that on the top dose all the animals treated with methylpentynol invariably showed abolition of the righting reflex, whereas on the lowest dose only rarely did more than one animal show a positive response. Only in those in which the narcotic activity of the compound was similar or greater than that of methylpentynol, was a more detailed examination made using a larger number of animals, except when it appeared necessary to assist correlation of narcotic activity with

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A STUDY OF THE ALKYLATION OF HYDRATROPONITRILE WITH BUTYL HALIDES¹

Cited by 3 publications

References 8 publications

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Addition and Substitution Reactions of Nitrile‐Stabilized Carbanions

Derivatives of Acetamide and Benzamide as Hypnotics

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A STUDY OF THE ALKYLATION OF HYDRATROPONITRILE WITH BUTYL HALIDES1

Cited by 3 publications

References 8 publications

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines1

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines1

Addition and Substitution Reactions of Nitrile‐Stabilized Carbanions

Derivatives of Acetamide and Benzamide as Hypnotics

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Product

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A STUDY OF THE ALKYLATION OF HYDRATROPONITRILE WITH BUTYL HALIDES¹

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹