title: New enolate-carbodiimide rearrangement in the concise synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines.
abstract: Three-step synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines involving NBS-mediated cyclization of N-(3-butenyl)ureas to 6-(bromomethyl)-2-iminourethanes, dehydrohalogenation and a novel rearrangement as a key step has been developed. The scope and limitations of the method, as well as the mechanism of the rearrangement, supported by kinetic studies and the isolation of N-(1-adamantyl)carbodiimide, are discussed. The final products, imino-analogues of well known piperidine-2,4-diones, are promising building blocks in the synthesis of bio-/pharmacological compounds.
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov 28, 119991, Moscow, Russian Federation. bubnov@ineos.ac.ru.
authors.forename: N Yu
authors.initials: NY
authors.lastname: Kuznetsov
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov 28, 119991, Moscow, Russian Federation. bubnov@ineos.ac.ru.
authors.forename: R M
authors.initials: RM
authors.lastname: Tikhov
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov 28, 119991, Moscow, Russian Federation. bubnov@ineos.ac.ru.
authors.forename: I A
authors.initials: IA
authors.lastname: Godovikov
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov 28, 119991, Moscow, Russian Federation. bubnov@ineos.ac.ru and Department of Inorganic Chemistry, Peoples' Friendship University of Russia, Miklukho-Maklay St., 6, Moscow 117198, Russian Federation.
authors.forename: V N
authors.initials: VN
authors.lastname: Khrustalev
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov 28, 119991, Moscow, Russian Federation. bubnov@ineos.ac.ru and N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russia.
authors.forename: Yu N
authors.initials: YN
authors.lastname: Bubnov