A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

Giovanni Appendino; Lavinia Cicione; Alberto Minassi

doi:10.1016/j.tetlet.2009.05.033

A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

Giovanni Appendino
, Lavinia Cicione
, Alberto Minassi

Department of Pharmaceutical Sciences

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

Abstract

The reaction of aldehydes with β-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed.

Original language	English
Pages (from-to)	5559-5561
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2009.05.033
Publication status	Published - 7 Oct 2009

Keywords

4-Hydroxycoumarin
Dehydroacetic acid
Indole
Multicomponent reactions

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10.1016/j.tetlet.2009.05.033

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title = "A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes",

abstract = "The reaction of aldehydes with β-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed.",

keywords = "4-Hydroxycoumarin, Dehydroacetic acid, Indole, Multicomponent reactions",

author = "Giovanni Appendino and Lavinia Cicione and Alberto Minassi",

note = "Funding Information: We thank MIUR (Fondi ex-40\%) for financial support. We are grateful to Mrs. Anna Maria Bottani for her help throughout this study.",

year = "2009",

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doi = "10.1016/j.tetlet.2009.05.033",

language = "English",

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T1 - A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

AU - Appendino, Giovanni

AU - Cicione, Lavinia

AU - Minassi, Alberto

N1 - Funding Information: We thank MIUR (Fondi ex-40%) for financial support. We are grateful to Mrs. Anna Maria Bottani for her help throughout this study.

PY - 2009/10/7

Y1 - 2009/10/7

N2 - The reaction of aldehydes with β-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed.

AB - The reaction of aldehydes with β-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed.

KW - 4-Hydroxycoumarin

KW - Dehydroacetic acid

KW - Indole

KW - Multicomponent reactions

UR - https://www.scopus.com/pages/publications/68949193007

U2 - 10.1016/j.tetlet.2009.05.033

DO - 10.1016/j.tetlet.2009.05.033

M3 - Article

SN - 0040-4039

VL - 50

SP - 5559

EP - 5561

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

Abstract

Keywords

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