Ueber die Einwirkung von Essigsäureanhydrid auf Säuren der Acetylenreihe

Michael, Arthur; Bucher, John E.

doi:10.1002/cber.18950280337

Cited by 44 publications

(28 citation statements)

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“…Already in 1895 Michael and Bucher reported the dimerization of phenylpropiolic acid upon prolonged boiling with acetic anhydride. 5 Twelve years later Pfeiffer and Möller described a similar reaction of ethyl phenylpropiolate under drastic conditions (200°C, sealed tube). 6 In the following period some preparative applications were published proving the scope of the reaction.…”

mentioning

confidence: 99%

The Photo-Dehydro-Diels-Alder Reaction: An Efficient Route to Naphthalenes

Wessig¹,

Müller²,

Kühn³

et al. 2005

Synthesis

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The photo-dehydro-Diels-Alder reaction (PDDA), a new photochemical route to naphthalenes is presented. The [4+2] cycloaddition takes place between 3-arylynones and arylacetylenes, in which these moieties may be located in two molecules (intermolecular PDDA, 1) or in the same molecule (intramolecular PDDA, 5 and 9). Especially the latter approach is attractive from a preparative point of view and permits a straightforward access to highly functionalized naphthalenes. The irradiation of unsymmetrical reactants 9 provides, in contrast to symmetrical reactants 5, two isomeric naphthalenes. We found that the regioselectivity can be easily influenced by suitably located substituents in the aromatic rings and by blocking undesired positions. Notably, the PDDA may be used for the preparation of binaphthyls, as shown by the formation of 14 and 16. The mechanism of the PDDA was elucidated by spectroscopic analyses and theoretical (DFT) calculations.

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mentioning

confidence: 99%

The Photo-Dehydro-Diels-Alder Reaction: An Efficient Route to Naphthalenes

Wessig¹,

Müller²,

Kühn³

et al. 2005

Synthesis

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“…The cyclized anhydride 252 was presumably formed via the isobenzene intermediate 251. 110 Often in these cycloaromatizations, mixtures of isomers are produced. A case in point is the intramolecular tetradehydro Diels-Alder reaction of the ether 253, which provides a mixture of 256 and 257 in a 75:25 ratio when heated in xylene.…”

Section: Scheme 39 Dehydro-diels-alder Additions With Vinylacetylene (10)mentioning

confidence: 99%

Allenes in Diels–Alder Cycloadditions

Hopf

Sherburn

2021

Synthesis

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For a long time, allenes—and cumulenic systems in general—played a relatively minor role in Diels–Alder cycloadditions. This situation has changed, since allenes are more readily available and as their unique stereochemical features in [4+2]cycloadditions are more widely recognized. This review presents a comprehensive overview of allenes in Diels–Alder processes using selected examples. Allenes in dienes, dienophiles and cycloadducts are covered, inter- and intramolecular Diels–Alder cycloadditions are discussed, and stereochemical features of the addition process are described. Areas of emerging importance are also covered, including allenic components in dehydro-Diels–Alder processes, and dendralenic allenes in Diels–Alder sequences for the rapid generation of target-relevant molecular complexity. Preparatively useful methods for allenic precursor synthesis are also discussed.1 Introduction2 Allenic Dienes2.1 Vinylallenes2.2 Bisallenes2.3 Cross-conjugated Allenes3 Allenic Dienophiles4 Intramolecular Diels–Alder Cycloadditions5 Allenic Cycloadducts6 Conclusions and Outlook

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“…The unique structural features as well as promising bioactivities of arylnaphthalene lactones have drawn considerable attention from synthetic chemists. Since the first synthesis of an arylnaphthalene lignan lactone skeleton in 1895 by the Bucher group (Michael and Bucher 1895) via the condensation of arylpropiolic Pharmacy,Gachon University,191 Hambakmoe-ro, Yeonsu-gu, Incheon 21936, Korea e-mail: dyshin@gachon.ac.kr acids, various synthetic approaches for arylnaphthalene lignan lactones have been designed and applied successfully. Major synthetic approaches include the intramolecular Diels-Alder reaction for the construction of an arylnaphthalene lactone from arylpropiolic anhydride Stevenson 1964, 1965;Maclean and Stevenson 1966;Block and Stevenson 1971;Stevenson 1970, 1971;Stevenson and Holmes 1971;Stevenson and Block 1971;Block and Stevenson 1973;Weber 1989, 1991;Anastas and Stevenson 1991;Park et al 2014).…”

Section: Introductionmentioning

confidence: 99%

Arylnaphthalene lactones: structures and pharmacological potentials

2021

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Natural arylnaphthalene lactones are representative lignans that are found in various dietary and medicinal plants. Their unique structural features and significant pharmacological activity have attracted considerable attention from both synthetic and medicinal chemists. Owing to their unique structural features such as relative rigid tetracyclic skeleton, structural diversity of more than five substituents, and no chiral center, arylnaphthalene lactones are recognized as a valuable scaffold for drug discovery, in addition to their significant pharmacological activities. This review covers the structures and isolation of all naturally occurring arylnaphthalene lactone congeners reported. Based on the aryl substituents, they were categorized as Type I and Type II and further classified according to the oxidation state of the ring and glycosylation level. Special attention has been paid to natural arylnaphthalene lactones owing to their broad spectrum of biological activities such as cytotoxic, antiplatelet, antiviral, anti-HIV, antifungal, neuroprotective, and anti-inflammatory properties. All the products were reorganized based on their biological activities, and selected data are presented.

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Ueber die Einwirkung von Essigsäureanhydrid auf Säuren der Acetylenreihe

Cited by 44 publications

References 0 publications

The Photo-Dehydro-Diels-Alder Reaction: An Efficient Route to Naphthalenes

The Photo-Dehydro-Diels-Alder Reaction: An Efficient Route to Naphthalenes

Allenes in Diels–Alder Cycloadditions

Arylnaphthalene lactones: structures and pharmacological potentials

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