Efficient Generation of ortho‐Naphthoquinone Methides from 1,4‐Epoxy‐1,4‐dihydronaphthalenes and Their Annulation with Allyl Silanes

Biobased C6-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

“…A series of O-substituted 1-hydroxymethyl-1,4-epoxy-1,4-dihydronaphthalenes was obtained by the interaction of the corresponding (2-hydroxymethyl)-5-methylfurans with benzyne (Scheme , eight examples, yield data were not provided). A variety of protecting groups were used.…”

Gold-Catalyzed Benzylic Azidation of Phthalans and Isochromans and Subsequent FeCl₃-Catalyzed Nucleophilic Substitutions

“…[9][10][11][12][13] We have continuously investigated the iron [14][15][16][17][18][19][20] -or gold [21][22][23] -catalyzed activation at the benzylic position of various skeletons accompanied by the benzylic C-O bond cleavage. During these investigations, the benzylic position of phthalan (1; n=1) as a benzene fused cyclic ether was found to be directly azidated in the presence of a gold catalyst and trimethylsilylazide (TMSN 3 ) without the C-O bond cleavage to give the 1-azido phthalan (2) (Chart 1).…”

A Strategy To Obtain o-Naphthoquinone Methides: Ag(I)-Catalyzed Cyclization of Enynones for the Synthesis of Benzo[h]chromanes and Naphthopyryliums

“…As a subtype of o-QMs, the o-naphthoquinone methides (o-NQMs) have been regarded as useful precursors for [4 + 2] annulation to synthesize benzo[h]chromanes, which are the core structure of many natural products and bioactive substances (Figure 1). 4 Compared with the o-QMs, fewer examples concerning the generation and application of o-NQMs have been reported, 5 largely due to the dearth of convenient routes to access the uniquely substituted onaphthol precursors. Therefore, the development of general strategies to obtain these useful o-NQM intermediates are of great importance.…”