1096497-66-3Relevant academic research and scientific papers
New synthetic approach for the construction of multisubstituted 2-acyl furans by the IBX-mediated cascade oxidation/cyclization of cis-2-En-4-yn-1-ols (IBX = 2-iodoxybenzoic acid)
Du, Xiangwei,Chen, Haoyi,Liu, Yuanhong
, p. 9495 - 9498 (2008)
A new approach for the construction of multisubstituted 2-acyl furans through cis-2-En-4-yn-1-ols (IBX=2-iodoxybenzoic acid)-mediated oxidation/cyclization in dimethyl sulfoxidse (DMSO) was developed. The results show that the introduction of an alkyl group at Cl provided a satisfactory yield of furan of 60% at 90°C. It is seen that IBX act as an electrophile to promote the cycloaddition of carbonyl group to the alkyne moiety. The furan derivatives are found to be useful synthetic intermediates for access to the compounds bearing biological activity. The studies also elucidate this reaction mechanism and extend the scope of synthetic utility of multisubstituted 2-acyl furans.
Highly efficient synthesis of multisubstituted 2-acyl furans via PIFA/I2-mediated oxidative cycloisomerization of cis -2-En-4-yn-1-ols
Du, Xiangwei,Chen, Haoyi,Chen, Yifeng,Chen, Jingjin,Liu, Yuanhong
supporting information; experimental part, p. 1010 - 1014 (2011/06/17)
A novel oxidative cycloisomerization of cis-enynols has been developed using a combination of hypervalent iodine(III) reagent, molecular iodine, and a base. This method offers an efficient synthesis of 2-acyl furans with diverse substitution patterns in a -regioselective manner under mild reaction conditions. A mechanistic proposal for these transformations involving alkyne activation by trifluoroacetylhypoiodite generated in situ is presented. Georg Thieme Verlag Stuttgart · New York.
