Reactivity of N-(omega-haloalkyl)-beta-lactams with regard to lithium aluminium hydride: novel synthesis of 1-(1-aryl-3-hydroxypropyl)aziridines and 3-aryl-3-(N-propylamino)propan-1-ols.
The reactivity of 4-aryl-1-(2-chloroethyl)azetidin-2-ones and 4-aryl-1-(3-bromopropyl)azetidin-2-ones with regard to lithium aluminium hydride has been evaluated for the first time. 4-Aryl-1-(2-chloroethyl)azetidin-2-ones were transformed into novel 1-(1-aryl-3-hydroxypropyl)aziridines through an unprecedented conversion of beta-lactams into 2,3-unsubstituted aziridine derivatives. Unexpectedly, 4-aryl-1-(3-bromopropyl)azetidin-2-ones underwent dehalogenation towards 3-aryl-3-(N-propylamino)propan-1-ols upon treatment with LiAlH(4). 1-(1-Aryl-3-hydroxypropyl)aziridines were further elaborated by means of ring opening reactions using benzyl bromide in acetonitrile towards 3-aryl-3-[N-benzyl-N-(2-bromoethyl)amino]propan-1-ols and using aluminium(iii) chloride in diethyl ether, affording 3-aryl-3-[N-(2-chloroethyl)amino]propan-1-ols.
D'hooghe
Matthias
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000, Ghent, Belgium.
Dekeukeleire
Stijn
S
De Kimpe
Norbert
N
D000433:1-Propanol / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry*; D017607:Aluminum Compounds / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D019163:Reducing Agents / Q000737:chemistry; D047090:beta-Lactams / Q000737:chemistry*
D000473:Alkanes; D017607:Aluminum Compounds; D001388:Aziridines; D018020:Lithium Compounds; D019163:Reducing Agents; D047090:beta-Lactams; C042073:lithium aluminum hydride; D000433:1-Propanol