title: A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline.
abstract: A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. charlesdennishall@gmail.com.
authors.forename: Olivier
authors.initials: O
authors.lastname: Nsengiyumva
authors.forename: Sadra
authors.initials: S
authors.lastname: Hamedzadeh
authors.forename: James
authors.initials: J
authors.lastname: McDaniel
authors.forename: Jocelyn
authors.initials: J
authors.lastname: Macho
authors.forename: Grant
authors.initials: G
authors.lastname: Simpson
authors.forename: Siva S
authors.initials: SS
authors.lastname: Panda
authors.forename: Khanh
authors.initials: K
authors.lastname: Ha
authors.forename: Iryna
authors.initials: I
authors.lastname: Lebedyeva
authors.forename: Hassan M
authors.initials: HM
authors.lastname: Faidallah
authors.forename: Manal Metgen
authors.initials: MM
authors.lastname: Al-Mohammadi
authors.forename: C Dennis
authors.initials: CD
authors.lastname: Hall
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000737:chemistry; D005021:Ethylamines / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D001688:Biological Products; D054659:Diketopiperazines; D004151:Dipeptides; D005021:Ethylamines; D014230:Triazoles; C012771:benzotriazole; D011392:Proline; C016162:triethylamine