TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=0002041182&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0002041182&partnerID=8YFLogxK
U2 - 10.1021/jo01052a054
DO - 10.1021/jo01052a054
M3 - Article
AN - SCOPUS:0002041182
SN - 0022-3263
VL - 27
SP - 1714
EP - 1717
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -