Synthesis and reactivity of some thiochroman-3,4-diones.

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Thiochroman-3,4-diones, which result from the reaction of thiochroman-4-ones with isoamyl nitrite, form fused heterocycles on reaction with 1,2-diamines and with p-anisaldehyde and ammonium acetate. Cyclopenta-[c][1]benzothiopyran-2-one, formed on reaction with dibenzyl ketone, yields a dibenzo[bd]thiopyran after cycloaddition of DMAD. With methyl magnesium iodide, a mixture of thiochroman-3-and 4-ols is fomed which was separated only after the selective dehydration of the 4-ol. The resulting 4-methylene derivative was isolated as the hetero Diels-Alder spiro-liked adduct.

LanguageEnglish
Pages7865-7878
Number of pages14
JournalTetrahedron
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jan 1994
Externally publishedYes

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Diamines
Cycloaddition
Cycloaddition Reaction
Ketones
Dehydration
Derivatives
thiopyran
4-anisaldehyde
ammonium acetate
magnesium iodide
isoamyl nitrite
methyl iodide

Cite this

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title = "Synthesis and reactivity of some thiochroman-3,4-diones.",
abstract = "Thiochroman-3,4-diones, which result from the reaction of thiochroman-4-ones with isoamyl nitrite, form fused heterocycles on reaction with 1,2-diamines and with p-anisaldehyde and ammonium acetate. Cyclopenta-[c][1]benzothiopyran-2-one, formed on reaction with dibenzyl ketone, yields a dibenzo[bd]thiopyran after cycloaddition of DMAD. With methyl magnesium iodide, a mixture of thiochroman-3-and 4-ols is fomed which was separated only after the selective dehydration of the 4-ol. The resulting 4-methylene derivative was isolated as the hetero Diels-Alder spiro-liked adduct.",
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Synthesis and reactivity of some thiochroman-3,4-diones. / Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark.

In: Tetrahedron, Vol. 50, No. 26, 01.01.1994, p. 7865-7878.

Research output: Contribution to journalArticle

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