title: 1,3-Diazepanes of natural product-like complexity from cyanamide-induced rearrangement of epoxy-delta-lactams.
abstract: A synthetic procedure toward 1,3-diazepane scaffolds of natural product-like complexity was developed for the construction of RNA-directed ligand libraries. A molecular building block was designed that combines the characteristics of RNA-binding natural products, including a high density of hydrogen bond donors and acceptors around a rigid, nonplanar scaffold with straightforward total-synthetic accessibility that permits extensive control over the chemical space. The synthesis of the 1,3-diazepane scaffold was achieved via an unprecedented cyanamide-induced rearrangement of epoxy-delta-lactams.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
authors.forename: Sanjay
authors.initials: S
authors.lastname: Dutta
authors.forename: Cody J
authors.initials: CJ
authors.lastname: Higginson
authors.forename: Bao T
authors.initials: BT
authors.lastname: Ho
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Rynearson
authors.forename: Sergey M
authors.initials: SM
authors.lastname: Dibrov
authors.forename: Thomas
authors.initials: T
authors.lastname: Hermann
mesh_terms: D001381:Azepines / Q000737:chemistry*; D003484:Cyanamide / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D004852:Epoxy Compounds; D007769:Lactams; D003484:Cyanamide