A Tandem Reaction of Benzyne with Functionalized Benzylidenephthalan To Afford Phenanthro[10,1-bc]furan

Abstract

A tandem reaction of benzyne with functionalized benzylidenephthalan for the synthesis of a variety of phenanthro[10,1-bc]furans has been achieved for the first time in moderate to good yields. The reaction mechanism involves a Diels–Alder reaction and an intermolecular nucleophilic addition reaction as the key steps.

The mechanism of the triple aryne–tetrazine reaction cascade: theory and experiment

“…We propose two possible mechanisms for the synthesis of rac - 8 consisting of a concerted ene-reaction or stepwise ene-type reaction of rac - 30 . 14 In both mechanisms, the two possible pathways support the existence of a currently non-isolable intermediate rac - 30 .…”

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

“…Besides, isoindolinediylidene-based compounds are the nuclei of pigments that cover the range from greenish yellow to orange, red and brown. 6 From the point of view of chemical reactivity, both phthalans and isoindolines are powerful building blocks for the syntheses of numerous classes of compounds (Scheme 1): benzylic amines 7 (a) and alcohols (b), 8 isoquinolin-1(2H)-ones (c), 9 phenanthro[10,1-bc]furans (d), 10 pyrazoles (e), 11 isochroman-3-ones (f), 7 isoindoles (g), 12 and isoindolinones (h). 13 Several procedures dedicated to the construction of such heterocycles have been developed.…”

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

“…[78][79][80] Furthermore, 1,3-dihydroisobenzofuran derivatives are functional building blocks in organic synthesis. [81][82][83][84] They've also been utilized to make phenanthrofurans, [85] isoquinolinones, [86] and chroman spiroketals (Figure 4). [87] Previously, reported reviews were based on synthetic approaches to 2,3-dihydrobenzofurans and natural products bearing the 2,3-dihydrobenzofuran core.…”