219755-76-7Relevant academic research and scientific papers
Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
Shimizu, Hisato,Yoshimura, Akira,Noguchi, Keiichi,Nemykin, Victor N.,Zhdankin, Viktor V.,Saito, Akio
, p. 531 - 536 (2018)
[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.
Efficient synthesis and subsequent transformations of phenylsulfanylbicyclo[2.2.2]octenones and phenylselenylbicyclo[2.2.2]octenones
Gao, Shih-Yu,Chittimalla, Santhosh Kumar,Chuang, Gary Jing,Liao, Chun-Chen
supporting information; experimental part, p. 1632 - 1639 (2009/07/09)
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.
The hetero Diels-Alder reactions of masked o-benzoquinones with nitroso compounds
Lin,Liao
, p. 1624 - 1625 (2007/10/03)
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.
One-pot stereoselective synthesis of tricyclic γ-lactones from 2-methoxyfuran and 2-methoxyphenols
Rao, Polisetti Dharma,Chen, Chien-Hsing,Liao, Chun-Chen
, p. 713 - 714 (2007/10/03)
A one-pot synthesis of the title compounds is achieved via highly facile Diels-Alder reactions of 2-methoxyfuran with masked o-benzoquinones.
