Medicinal nitro-compounds. Part II. Search for ortho-interactions in tumour-inhibitory 2,4-dinitrophenylaziridines

G. A M Butchart, M. F G Stevens, Brian C Gunn

Research output: Contribution to journalArticle

Abstract

The 1-(2,4-dinitrophenyl)aziridines (1) and (2) behave as alkylating agents and undergo ring-opening under a range of mild conditions. With organic acids in toluene, 1-(2,4-dinitrophenyl) aziridine (1) yields esters of 2-(2,4-dinitroanilino)ethanol (7)-(13). In strong acids (without solvent) the esters are accompanied by polymer (18). 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) (2) similarly yields esters (14) or (15) in acetic or propionic acids, but polymer (19) in formic acid. Ring opening of the aziridine (1) in mineral acids, in alcohols containing acids, or in alcohols containing alkyl iodides is influenced by the nucleophilicity of the attacking reagent. A series of ethylenediamines (28)-(33) was prepared from the aziridines (1) and (2) and amines without a catalyst being present, but in pyridine, or 3- or 4-aminopyridine, the aziridine (1) afforded polymer (18). The aziridine (1) on acidic or basic alumina in boiling toluene afforded a product identified as bis-[2-(2,4-dinitroanilino)ethyl] ether (35) on the basis of its spectroscopic properties, whereas photolysis in methanol led to ring opening and formation of N-(2-methoxyethyl)-2,4-dinitroaniline (26).

Original languageEnglish
Pages (from-to)956-963
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number10
Publication statusPublished - 1975

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Nitro Compounds
Tumors
Polymers
Esters
formic acid
Toluene
Ethylenediamines
Acids
Aziridines
Alcohols
4-Aminopyridine
Aluminum Oxide
Alkylating Agents
Organic acids
Propionates
Photolysis
Iodides
Acetic Acid
Ether
Boiling liquids

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title = "Medicinal nitro-compounds. Part II. Search for ortho-interactions in tumour-inhibitory 2,4-dinitrophenylaziridines",
abstract = "The 1-(2,4-dinitrophenyl)aziridines (1) and (2) behave as alkylating agents and undergo ring-opening under a range of mild conditions. With organic acids in toluene, 1-(2,4-dinitrophenyl) aziridine (1) yields esters of 2-(2,4-dinitroanilino)ethanol (7)-(13). In strong acids (without solvent) the esters are accompanied by polymer (18). 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) (2) similarly yields esters (14) or (15) in acetic or propionic acids, but polymer (19) in formic acid. Ring opening of the aziridine (1) in mineral acids, in alcohols containing acids, or in alcohols containing alkyl iodides is influenced by the nucleophilicity of the attacking reagent. A series of ethylenediamines (28)-(33) was prepared from the aziridines (1) and (2) and amines without a catalyst being present, but in pyridine, or 3- or 4-aminopyridine, the aziridine (1) afforded polymer (18). The aziridine (1) on acidic or basic alumina in boiling toluene afforded a product identified as bis-[2-(2,4-dinitroanilino)ethyl] ether (35) on the basis of its spectroscopic properties, whereas photolysis in methanol led to ring opening and formation of N-(2-methoxyethyl)-2,4-dinitroaniline (26).",
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Medicinal nitro-compounds. Part II. Search for ortho-interactions in tumour-inhibitory 2,4-dinitrophenylaziridines. / Butchart, G. A M; Stevens, M. F G; Gunn, Brian C.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 10, 1975, p. 956-963.

Research output: Contribution to journalArticle

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T1 - Medicinal nitro-compounds. Part II. Search for ortho-interactions in tumour-inhibitory 2,4-dinitrophenylaziridines

AU - Butchart, G. A M

AU - Stevens, M. F G

AU - Gunn, Brian C

PY - 1975

Y1 - 1975

N2 - The 1-(2,4-dinitrophenyl)aziridines (1) and (2) behave as alkylating agents and undergo ring-opening under a range of mild conditions. With organic acids in toluene, 1-(2,4-dinitrophenyl) aziridine (1) yields esters of 2-(2,4-dinitroanilino)ethanol (7)-(13). In strong acids (without solvent) the esters are accompanied by polymer (18). 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) (2) similarly yields esters (14) or (15) in acetic or propionic acids, but polymer (19) in formic acid. Ring opening of the aziridine (1) in mineral acids, in alcohols containing acids, or in alcohols containing alkyl iodides is influenced by the nucleophilicity of the attacking reagent. A series of ethylenediamines (28)-(33) was prepared from the aziridines (1) and (2) and amines without a catalyst being present, but in pyridine, or 3- or 4-aminopyridine, the aziridine (1) afforded polymer (18). The aziridine (1) on acidic or basic alumina in boiling toluene afforded a product identified as bis-[2-(2,4-dinitroanilino)ethyl] ether (35) on the basis of its spectroscopic properties, whereas photolysis in methanol led to ring opening and formation of N-(2-methoxyethyl)-2,4-dinitroaniline (26).

AB - The 1-(2,4-dinitrophenyl)aziridines (1) and (2) behave as alkylating agents and undergo ring-opening under a range of mild conditions. With organic acids in toluene, 1-(2,4-dinitrophenyl) aziridine (1) yields esters of 2-(2,4-dinitroanilino)ethanol (7)-(13). In strong acids (without solvent) the esters are accompanied by polymer (18). 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) (2) similarly yields esters (14) or (15) in acetic or propionic acids, but polymer (19) in formic acid. Ring opening of the aziridine (1) in mineral acids, in alcohols containing acids, or in alcohols containing alkyl iodides is influenced by the nucleophilicity of the attacking reagent. A series of ethylenediamines (28)-(33) was prepared from the aziridines (1) and (2) and amines without a catalyst being present, but in pyridine, or 3- or 4-aminopyridine, the aziridine (1) afforded polymer (18). The aziridine (1) on acidic or basic alumina in boiling toluene afforded a product identified as bis-[2-(2,4-dinitroanilino)ethyl] ether (35) on the basis of its spectroscopic properties, whereas photolysis in methanol led to ring opening and formation of N-(2-methoxyethyl)-2,4-dinitroaniline (26).

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