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. 2011 Aug 2;16(8):6470-80.
doi: 10.3390/molecules16086470.

Expeditious entry to novel 2-methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-chloro-4-hydroxychromen-2-one and propargylic alcohols

Noel Nebra  1 , Alba E Díaz-Álvarez, Josefina Díez, Victorio Cadierno
Affiliations

Expeditious entry to novel 2-methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-chloro-4-hydroxychromen-2-one and propargylic alcohols

Noel Nebra et al. Molecules. .

Abstract

A catalytic system consisting of the ruthenium(II) complex [Ru(η³-2-C3H4Me)(CO)(dppf)][SbF6] (dppf=1,1'-bis(diphenylphosphino)ferrocene) and trifluoroacetic acid has been used to promote the coupling of secondary propargylic alcohols with 6-chloro-4-hydroxychromen-2-one. The reactions afforded unusual 2-methylene-2,3-dihydrofuro[3,2-c]chromen-2-ones in good yields.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The furo[3,2-c]chromen-2-one skeleton.
Scheme 1
Scheme 1
Direct synthesis of furans from alkynols and 1,3-dicarbonyl compounds.
Figure 2
Figure 2
Structures of compounds 4 and 5.
Scheme 2
Scheme 2
Catalytic synthesis of compound 4a under classical thermal conditions.
Figure 3
Figure 3
ORTEP-type view of the structure of compound 4a showing the crystallographic labelling scheme. Thermal ellipsoids are drawn at the 20% probability level.
Scheme 3
Scheme 3
Catalytic synthesis of compound 4a–d under MW-irradiation.
Scheme 4
Scheme 4
Synthesis of the furo[3,2-c]chromen-2-one 5b.
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