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.docVIP

Molecules 2011, 16, 6470-6480; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article 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, Alba E. Díaz-álvarez, Josefina Díez and Victorio Cadierno * Departamento de Química Orgánica e Inorgánica, IUQOEM-CSIC, Facultad de Química, Universidad de Oviedo, E-33071 Oviedo, Spain * Author to whom correspondence should be addressed; E-Mail: vcm@uniovi.es; Tel.: +34-985-103-453; Fax: +34-985-103-446. Received: 14 July 2011; in revised form: 27 July 2011 / Accepted: 28 July 2011 / Published: 2 August 2011 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. Keywords: chromen-2-ones; furochromen-2-ones; propargylic alcohols; ruthenium catalysts; propargylation; cycloisomerization 1. Introduction Chromen-2-ones (coumarins) constitute an important family of heterocyclic compounds of natural origin which have attracted considerable attention for many years due to their versatile applications [1-4]. Among them, furochromen-2-ones (furocoumarins), tricyclic systems in which a furan ring is fused to the chromen-2-one unit, are of particular interest since they exhibit potent biological and pharmacological activity [5-8]. Although several methods of synthesis are presently known [7,8], new approaches for the rapid and selective construction of furochromen-2-one scaffolds are still highly desirable. In this context, recent efforts by different groups have been focused in the one-pot synth