Acid catalysis of the Claisen rearrangement. 2. Formation of the benzofurobenzopyran and benzofuro[3,2-b]benzofuran skeletons from 1,4-bis(aryloxy)-2-butynes
About: This article is published in Journal of Organic Chemistry.The article was published on 1978-09-01. It has received 27 citations till now. The article focuses on the topics: Claisen rearrangement & Benzofuran.
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TL;DR: The thermal rearrangement of 2,4-di(N-aryl)amino-1,3,5-triazin-6yl-prop-2-ynyl ethers 1 yield a mixture of 6-methyleneimidazo(1,2-a)-1, 3, 5-triazine-4-one 6 and 6-methylimidazo (1, 2-a) 1, 3.5-trifluroacetate 4-one 7 at room temperature, whereas under the influence of mercuric trif
4 citations
TL;DR: A proton nmr follow-up provided conclusive evidence for the involvement of two sequential Claisen rearrangements in the thermal rearrangement of 1,4-diaryloxy-2-butnes 1 to 11a-methylpterocarpans 3 as discussed by the authors.
4 citations
28 Jun 2018
TL;DR: In this article, the application of iridium(I) and ruthenium(II) complexes to the synthesis of complex organic products has been discussed in both catalytic and asymmetric fashion.
Abstract: The application of transition metals to the synthesis complex organic products has become an extremely important facet of chemistry in the last few decades. Such metal complexes exhibit remarkable activity in the construction of new carbon-carbon or carbon-heteroatom bonds in both catalytic and asymmetric fashion. The advance in organometallic chemistry has allowed chemists to access new structural scaffolds while also minimizing the use of stoichiometric reagents. The document herein details the application of iridium(I) and ruthenium(II) complexes to the synthesis of complex organic products. Iridium(I) compounds display good activity in the chemoselective isomerization of di(allyl) ethers and carbonates to access allyl vinyl compounds which are classic substrates for Claisen rearrangements. Ruthenium(II) catalysis can provide α,β-substituted-γ,δ-unsaturated aldehydes and amides from allyl vinyl species such as allyl vinyl ethers, carbonatres, silyl enol ethers and allyl acetates. Our methodology was utilized in the construction of the active core of a potential cancer therapeutic, actinoranone.
4 citations
TL;DR: A number of quinolone-annulated pentacycles have been regioselectively synthesized in 90-95% yields by sequential Claisen rearrangements.
4 citations
TL;DR: In this article, the synthesis of 1,8 naphthyridine-annulated polyheterocycles containing oxygen, nitrogen, and sulfur has been achieved by thionation and sequential Claisen rearrangement.
4 citations