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Relevant academic research and scientific papers

Diels-Alder and Michael addition reactions of indoles with masked o-benzoquinones: Synthesis of highly functionalized hydrocarbazoles and 3-arylindoles

Highly functionalized hydrocarbazoles and 3-arylindoles are prepared from commercially available 2-methoxyphenols and indoles.

Cyclopropane ring-opening of tricyclo[3.3.0.02,8]octan-3-ones: a quick access to bicyclo[3.2.1]octanones from 2-methoxyphenols

We herein report an efficient and rapid strategy for the synthesis of highly functionalized bicyclo[3.2.1]octanones via sequential reactions: Diels-Alder reaction of MOB-ODPM rearrangement-reductive cleavage of cyclopropane, and its application to synthes

Sonochemical cycloadditions of o-quinones. The search for a cation radical pathway

Diels-Alder cycloadditions of an o-quinone monoketal with different furans, under argon, are considerably accelerated by ultrasonic irradiation. Moreover, these sonochemical reactions are regiospecific and proceed with a high diastereoselectivity. The res

Efficient synthesis and subsequent transformations of phenylsulfanylbicyclo[2.2.2]octenones and phenylselenylbicyclo[2.2.2]octenones

Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones 2 with phenyl vinyl sulfide and phenyl vinyl selenide furnished highly functionalized bicyclo[2.2.2]octenone derivatives 3 and 4, respectively, in excellent regio- and stereoselectivities and yields up to 90%. The bicyclo[2.2.2]octenone derivatives 3 with the sulfur functionality were subjected to an oxidation-elimination process to furnish bicyclo[2.2.2] octadienone systems 7 in good yields. During the reduction process, the Diels-Alder adducts 3e and 4e led to 8, whereas the carbon-centered radicals generated from the other adducts 3a-d and 4a-d provided various rearranged products 9-13 depending on the substitution pattern and reagents utilized (Raney-Ni or n-Bu3SnH). Surprisingly these radicals showed preference for the carbonyl functionality to the olefinic double bond, leading to interesting rearrangement reactions of mechanistic importance and possible synthetic utility. Interestingly the alcohols obtained from the reduction of Diels-Alder adducts 3a-d underwent desulfurization smoothly to give desulfurized products in high yields; thus a detoured method of "reduction- desulfurization-oxidation" provides an entry to desulfurized bicyclo[2.2.2]octenones without rearrangement.

Thiophenes act as dienophiles in novel cycloadditions with masked o-benzoquinones

Highly selective Diels-Alder reactions of masked o-benzoquinones with thiophenes are described.

The hetero Diels-Alder reactions of masked o-benzoquinones with nitroso compounds

The first examples of hetero Diels-Alder reaction of masked o-benzoquinones with nitroso dienophiles leading to novel and highly functionalized heterocycles, which are potential intermediates for nitrogenous natural products are reported.

Diels-Alder reactions of masked o-benzoquinones with electron-rich dienophiles. Highly regio- and stereoselective synthesis of bicyclo [2.2.2]octenone derivatives

Highly regio- and stereoselective Diels-Alder reactions of masked o- benzoquinones with electron-rich dienophiles such as benzyl vinyl ether, dihydrofuran, phenyl vinyl sulfide and styrene that provide easy access to bicyclo[2.2.2]octenones are described.

Highly functionalized bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C60

The Diels-Alder reactions of masked obenzoquinones (MOBs) with [60]fullerene, affording novel and highly functionalized bicyclo[2.2.2]-octenone-fused [60]fullerene derivatives, are described.

One-pot stereoselective synthesis of tricyclic γ-lactones from 2-methoxyfuran and 2-methoxyphenols

A one-pot synthesis of the title compounds is achieved via highly facile Diels-Alder reactions of 2-methoxyfuran with masked o-benzoquinones.