Studies on Antitumor Substances. XII. Synthesis of Bis (2, 3-epoxypropyl) amine Derivatives and the Reaction with Some Nucleophiles

• Published in: Chemical & pharmaceutical bulletin Vol. 19; no. 10; pp. 2003 - 2008
• Main Authors: FUJINO, YOKO, FURUKAWA, MITSURU, NAKAO, TORU, SUGITA, MAKOTO, HAYASHI, SEIGORO
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 01.10.1971; Japan Science and Technology Agency
• Subjects: Amines - chemical synthesis; Antineoplastic Agents - chemical synthesis; Benzene Derivatives - chemical synthesis; Chemical Phenomena; Chemistry; Ethers, Cyclic - chemical synthesis; Piperazines - chemical synthesis
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.19.2003

Several bis (2, 3-epoxypropyl) amine derivatives were successfully synthesized by the modification of Homer's method. N, N'-Bis (2, 3-epoxypropyl) piperazine and p-bis (2, 3-epoxypropoxy) benzene were attempted to react with thiols, amines and phenol, and the corresponding ring opening compounds of the epoxide ring were obtained in good yields, respectively. N, N'-Bis (2, 3-epoxypropyl) piperazine and p-bis (2, 3-epoxypropoxy) benzene also reacted with diethyl malonate to give N, N'-bis (γ-ethoxycarbonyl-γ-butyrolacton-α-yl) methyl piperazine and p-bis (γ-ethoxycarbonyl-γ-butyrolacton-α-yl) methoxy benzene, respectively.