New DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) Assisted One-Pot Synthesis of 2,8-Disubstituted 4H-1-Benzopyran-4-ones

Carlo Riva; Carlo De Toma; Leandro Donadel; Carlo Boi; Renzo Pennini; Gianni Motta; Amedeo Leonardi

doi:10.1055/s-1997-1168

Synthesis 1997; 1997(2): 195-201
DOI: 10.1055/s-1997-1168

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New DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) Assisted One-Pot Synthesis of 2,8-Disubstituted 4H-1-Benzopyran-4-ones

Carlo Riva^* , Carlo De Toma, Leandro Donadel, Carlo Boi, Renzo Pennini, Gianni Motta, Amedeo Leonardi

^*Pharmaceutical R. & D. Division, Recordati S.p.A., Via Civitali 1, I-20148, Milano, Italy, Fax +39(2)48709017

Abstract

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2-Hydroxy-3-(alkoxycarbonyl or prop-1-enyl)phenyl alkyl ketones are easily converted into 2,8-disubstituted (3-methyl)-4H-1-benzopyran-4-ones through a new DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) assisted one-pot synthesis, by reaction with aroyl or alkanoyl chlorides or anhydrides. The method is simple, mild and convenient as compared to the existing multistep procedures.

1,8-diazabicyclo[5.4.0]undec-7-ene - 4-oxo-4H-1-benzopyran-8-carboxylates - one-pot synthesis - 2,8-distubstituted-4H-1-benzopyran-4-ones - 2-hydroxy-3-(1-oxoalkyl)-benzoates

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