title: Synthesis and characterization of 5-substituted 1,3-diazacyclohexane derivatives
abstract: Three synthetic routes to 5-substituted 1,3-diazacyclohexane derivatives 1 are reported. The first method involves treatment of 1, 3-diaminopropan-2-ol 2 with paraformaldehyde to yield 5-hydroxy-1, 3-diazacyclohexane 3. A second method is based on the condensation of 2-bromo-2-nitro-1,3-propanediol with tert-butylamine and formaldehyde to yield 1,3-di-tert-butyl-5-bromo-5-nitro-1, 3-diazacyclohexane 22. The third method relies on the cycloalkylation of methylenebisacetamide with 3-chloro-2-chloromethyl-2-propene to provide 5-exomethylene-1, 3-diacetyl-1,3-diazacyclohexane 28. Functional group manipulations of 3, 22, and 28 provide a number of novel 1,3-diazacyclohexanes functionalized at the 5-position.
authors.affiliation: Laboratory for the Structure of Matter, Naval Research Laboratory, 4555 Overlook Avenue, SW, Washington DC 20375, USA.
authors.initials: T
authors.lastname: Axenrod
authors.initials: J
authors.lastname: Sun
authors.initials: KK
authors.lastname: Das
authors.initials: PR
authors.lastname: Dave
authors.initials: F
authors.lastname: Forohar
authors.initials: M
authors.lastname: Kaselj
authors.initials: NJ
authors.lastname: Trivedi
authors.initials: RD
authors.lastname: Gilardi
authors.initials: JL
authors.lastname: Flippen-Anderson