Reactions of 2,3,5-Trichloro-4,4-ethylenedioxy-2-cyclopentenone with Some Ambident Nucleophiles. Sterically Loaded Functionalized 6-Azabicyclo[3.1.0]hex-5-enes

Autor:	R. R. Akhmetvaleev, Mansur S. Miftakhov, N. A. Ivanova, F. G. Usmanova, G. A. Shavaleeva
Rok vydání:	2005
Předmět:	Chemistry Organic Chemistry General Medicine Oxime Medicinal chemistry chemistry.chemical_compound Hydroxylamine Nucleophile Dioxolane Potassium thiocyanate Organic chemistry Ethylenedioxy Tetrahydrofuran Derivative (chemistry)
Zdroj:	ChemInform. 36
ISSN:	1522-2667 0931-7597
Popis:	2,3,5-Trichloro-4,4-ethylenedioxy-2-cyclopentenone reacted with sodium azide in tetrahydrofuran to give the expected 3-azido derivative which was converted into 1,3-dichloro-4,4-ethylenedioxy-6-azabicyclo-[3.1.0]hex-5-en-2-one and 3-amino-2,5-dichloro-4,4-ethylenedioxy-2-cyclopentenone on heating in chloroform. The reaction of 2,3,5-trichloro-4,4-ethylenedioxy-2-cyclopentenone with potassium thiocyanate, depending on the conditions, afforded the corresponding 3-thiocyanato derivative or symmetric sulfide. Treatment of the title compound with hydroxylamine resulted in opening of the dioxolane ring with simultaneous formation of oxime via replacement of chlorine at the neighboring sp 2-carbon atom.
Databáze:	OpenAIRE
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