title: Irreversible Conjugation of Aldehydes in Water To Form Stable 1,2,4-Oxadiazinan-5-ones.
abstract: A new, irreversible aldehyde conjugation reaction in aqueous media was developed. α-Aminooxy acetohydrazides undergo irreversible condensation reactions with aliphatic, aromatic, or unsaturated aldehydes and isatins in a mixture of acetonitrile and acetate buffer at pH 4 to yield 1,2,4-oxadiazinan-5-one heterocycles in excellent isolated yields (40-99%). This class of heterocycles proved to be hydrolytically stable throughout a wide range of temperatures and pH (4.5-7).
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich , 8093 Zürich, Switzerland.|Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Alexandre F
authors.initials: AF
authors.lastname: Trindade
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich , 8093 Zürich, Switzerland.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode