e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of substituted 2H [1] benzopyrans from coumarins and chromones

A Alberola, AG Ortega, R Pedrosa…

Index: Alberola; Ortega; Pedrosa; et al. Journal of Heterocyclic Chemistry, 1983 , vol. 20, # 3 p. 715 - 718

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Citation Number: 12

Abstract

Abstract A convenient route to substituted 2H [1] benzopyrans is described in which trialkylaluminium compounds are added to coumarins or chromones and the resultant Z-2-(3- hydroxy-1-propenyl) phenols are converted by thermal cyclization in the presence of silica gel to 2H [l] benzopyrans.

(Z)-2-(3-ethyl-3-hydroxy-2-methylpent-1-en-1-yl)phenol Structure

(Z)-2-(3-ethyl-...

~70%

2,2-diethyl-3-methylchromene Structure

2,2-diethyl-3-m...

2H-1-Benzopyran-2-one,3-methyl- Structure

2H-1-Benzopyran...

~%

2,2-diethyl-3-methylchromene Structure

2,2-diethyl-3-m...

(Z)-2-(3-ethyl-3-hydroxy-2-phenylpent-1-en-1-yl)phenol Structure

(Z)-2-(3-ethyl-...

~59%

2,2-diethyl-3-phenylchromene Structure

2,2-diethyl-3-p...

2H-1-Benzopyran-2-one,3-phenyl- Structure

2H-1-Benzopyran...

~%

2,2-diethyl-3-phenylchromene Structure

2,2-diethyl-3-p...

3-phenylpropanoyl 3-phenylpropanoate Structure

3-phenylpropano...

Salicylaldehyde Structure

Salicylaldehyde

~45%

3-benzylchromen-2-one Structure

3-benzylchromen...

(Z)-2-(3-hydroxyprop-1-en-1-yl)phenol Structure

(Z)-2-(3-hydrox...

~44%

2H-chromene Structure

Coumarin Structure

~%

2H-chromene Structure

3-ethyl-1c-(2-hydroxy-phenyl)-penten-(1)-ol-(3) Structure

3-ethyl-1c-(2-h...

~59%

2,2-diethylchromene Structure

2,2-diethylchromene

Coumarin Structure

~%

2,2-diethylchromene Structure

2,2-diethylchromene

(E)-β-[2-hydroxyphenylethylene]benzeneethanol Structure

(E)-β-[2-hydrox...

~46%

3(2H)-isoflavene Structure

3(2H)-isoflavene

2H-1-Benzopyran-2-one,3-phenyl- Structure

2H-1-Benzopyran...

~%

3(2H)-isoflavene Structure

3(2H)-isoflavene