Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)

George R. Pettit; Joseph A. Settepani

doi:10.1021/jo01052a054

Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)

George R. Pettit, Joseph A. Settepani

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Abstract

A Mannich-type reaction involving bis(2-chloroethyl)amine, formaldehyde, and several amides has been investigated. Bis(2-chloroethyl)amine was shown to condense in ethanol-formalin solution with phthalimide, saccharin, isatin, and isatin thiosemicarbazone to yield (51-89%) the corresponding nitrogen mustard Mannich bases II, IV, and VI. The reaction was found to follow other courses under acidic conditions. Formation of V-methylbis(2-chloroethyl)amine and conversion of saccharin to alkoxymethylene (VII) and bismethylene (VIII) derivatives occurred in acidic media.

Original language	English (US)
Pages (from-to)	1714-1717
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	27
Issue number	5
DOIs	https://doi.org/10.1021/jo01052a054
State	Published - May 1 1962
Externally published	Yes

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Organic Chemistry

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title = "Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)",

abstract = "A Mannich-type reaction involving bis(2-chloroethyl)amine, formaldehyde, and several amides has been investigated. Bis(2-chloroethyl)amine was shown to condense in ethanol-formalin solution with phthalimide, saccharin, isatin, and isatin thiosemicarbazone to yield (51-89%) the corresponding nitrogen mustard Mannich bases II, IV, and VI. The reaction was found to follow other courses under acidic conditions. Formation of V-methylbis(2-chloroethyl)amine and conversion of saccharin to alkoxymethylene (VII) and bismethylene (VIII) derivatives occurred in acidic media.",

author = "Pettit, {George R.} and Settepani, {Joseph A.}",

year = "1962",

month = may,

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T1 - Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)

AU - Pettit, George R.

AU - Settepani, Joseph A.

PY - 1962/5/1

Y1 - 1962/5/1

N2 - A Mannich-type reaction involving bis(2-chloroethyl)amine, formaldehyde, and several amides has been investigated. Bis(2-chloroethyl)amine was shown to condense in ethanol-formalin solution with phthalimide, saccharin, isatin, and isatin thiosemicarbazone to yield (51-89%) the corresponding nitrogen mustard Mannich bases II, IV, and VI. The reaction was found to follow other courses under acidic conditions. Formation of V-methylbis(2-chloroethyl)amine and conversion of saccharin to alkoxymethylene (VII) and bismethylene (VIII) derivatives occurred in acidic media.

AB - A Mannich-type reaction involving bis(2-chloroethyl)amine, formaldehyde, and several amides has been investigated. Bis(2-chloroethyl)amine was shown to condense in ethanol-formalin solution with phthalimide, saccharin, isatin, and isatin thiosemicarbazone to yield (51-89%) the corresponding nitrogen mustard Mannich bases II, IV, and VI. The reaction was found to follow other courses under acidic conditions. Formation of V-methylbis(2-chloroethyl)amine and conversion of saccharin to alkoxymethylene (VII) and bismethylene (VIII) derivatives occurred in acidic media.

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DO - 10.1021/jo01052a054

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Antineoplastic Agents. VI. Mannich Base Nitrogen Mustards (Part B)

Abstract

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