Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

David S. Clarke; Christopher D. Gabbutt; John D. Hepworth; B. Mark Heron

doi:10.1016/j.tetlet.2005.06.058

Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

David S. Clarke, Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH₄ in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO ₃H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.

Original language	English
Pages (from-to)	5515-5519
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	33
Early online date	1 Jul 2005
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.058
Publication status	Published - 15 Aug 2005
Externally published	Yes

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title = "Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones",

abstract = "3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.",

keywords = "Chroman-4-ones, Chromones, Conjugate reduction, Flavones, Rearrangement",

author = "Clarke, {David S.} and Gabbutt, {Christopher D.} and Hepworth, {John D.} and Heron, {B. Mark}",

year = "2005",

month = aug,

day = "15",

doi = "10.1016/j.tetlet.2005.06.058",

language = "English",

volume = "46",

pages = "5515--5519",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

AU - Clarke, David S.

AU - Gabbutt, Christopher D.

AU - Hepworth, John D.

AU - Heron, B. Mark

PY - 2005/8/15

Y1 - 2005/8/15

N2 - 3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.

AB - 3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.

KW - Chroman-4-ones

KW - Chromones

KW - Conjugate reduction

KW - Flavones

KW - Rearrangement

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U2 - 10.1016/j.tetlet.2005.06.058

DO - 10.1016/j.tetlet.2005.06.058

M3 - Article

AN - SCOPUS:22144433401

VL - 46

SP - 5515

EP - 5519

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 33

ER -

Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

Abstract

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