New tandem Ugi/intramolecular Diels-Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives.

ABSTRACT: A new tandem sequence involving the Ugi reaction and Diels-Alder [4 + 2] cycloaddition based on vinylfuran and 1,3-butadienylfuran derivatives was designed and studied. It was found that in the case of 3-(furan-2-yl)acrylaldehyde, a one-pot Ugi reaction and intramolecular Diels-Alder vinylarene (IMDAV) reaction leads to the formation of the insufficiently studied furo[2,3-f]isoindole derivatives. Ugi adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, and an amine spontaneously underwent the IMDAV reaction with a high level of stereoselectivity, leading to single pairs of enantiomers of 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindole core in excellent yields. Under the same conditions, the (2E,4E)-5-(furan-2-y

SUBMITTER: Horak YI 

PROVIDER: S-EPMC11878150 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature