Process for the preparation of 1,2-dioxetane compounds and...

C - Chemistry – Metallurgy – 07 – D

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C07D 321/00 (2006.01) C07D 405/04 (2006.01) C07F 7/18 (2006.01) C07F 9/655 (2006.01) C07H 15/26 (2006.01)

Patent

CA 2223293

A process is provided for the preparation of a variety of triggerable dioxetanes bearing alkoxy, alkenyloxy, alkynyloxy, arlyoxy, aralkyloxy or acyloxy substituents from a common intermediate along with sulfur-substituted dioxetanes and vinyl sulfide compounds used as intermediates. Alkoxy, alkenyloxy, alkynyloxy, arlyoxy, aralkyloxy or acyloxy substituted dioxetanes are useful in detecting activating agents and in assays such as immunoassays and nucleic acid hybridization assays. The sulfur-substituted dioxetanes additionally are useful for producing chemiluminescence. The novel process involves conversion of a vinyl sulfide compound to a sulfur-substituted dioxetane, reacting the sulfur-substituted dioxetane with an electrophilic agent and a hydroxylic compound or salt thereof and forming the alkoxy, alkenyloxy, alkynyloxy, arlyoxy, aralkyloxy or acyloxy-substituted dioxetane.

L'invention présente un procédé pour la préaparation d'une variété de dioxétanes déclenchables portant des substituants alcoxy, alcényloxy, alcynyloxy, arlyoxy, aralkyloxy ou acyloxy provenant d'une intermédiare commun avec des dioxétanes sulfo-substitués et des composés de sulfure de vinyle utilisés comme intermédiaires. Les dioxétanes substitués alcoxy, alcényloxy, alcynyloxy, arlyoxy, aralkyloxy ou acyloxy sont utiles pour détecter des agents activants et dans des dosages tels que des immunodosages et des dosages d'hybridation d'acide nucléique. Les dioxétanes sulfo-substitués sont en outre utiles pour la production de luminescence chimique. Ce nouveau procédé consiste à convertir un composé de sulfure de vinyle en un dioxétane sulfo-substitué, à faire réagir le dioxétane sulfo-substitué avec un agent électrophile et un composé hydroxylique ou un sel de celui-ci et à former le dioxétane substitué alcoxy, alcényloxy, alcynyloxy, arlyoxy, aralkyloxy ou acyloxy.

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