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

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• 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

• yields. The studied tandem Ugi and intramolecular Diels–Alder reactions allow high substituent variation in the named isoindoles. Keywords: 1,3-butadienylfuran; furo[2,3-f]isoindole; intramolecular Diels–Alder reaction; isoindole; one-pot; Ugi reaction; vinylfuran; Introduction Energy-saving and

• present work, the new tandem sequence involving an Ugi reaction and Diels–Alder [4 + 2] cycloaddition based on vinylfuran, 1,3-butadienylfuran derivatives was designed and studied. Results and Discussion To carry out an intramolecular Diels–Alder reaction, we tested (E)-3-(furan-2-yl)acrylaldehyde (1a) in

Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers

• Florin M. Istrate and
• Fabien Gagosz

Beilstein J. Org. Chem. 2011, 7, 878–885, doi:10.3762/bjoc.7.100

• (entries 8–13). A large variety of substituents were tolerated including primary, secondary or tertiary alkyl groups and even a vinyl or a phenyl group. However, a poor yield (17%) was obtained when compound 6l was used as the substrate, due to the facile polymerization of the corresponding vinylfuran 7l

Synthesis of Ru alkylidene complexes

• Renat Kadyrov and
• Anna Rosiak

Beilstein J. Org. Chem. 2011, 7, 104–110, doi:10.3762/bjoc.7.14

• (Waters) was used. All solvents used were anhydrous grade purchased from Aldrich. Commercially available compounds were used without further purification. 2-Vinylthiophene [16], 2-vinylfuran [17], 1-vinylcyclohexene [18], 1-vinylcyclopentene [18] and nopadiene [19] were prepared according to known