Diels-Alder Chemistry Research Articles

Reaction of 2-Acetoxy-3-chloro and 2,3-Diacetoxy Naphthoquinones with 1,3-Dioxy and 1,1,3-Trioxy Butadienes

Reaction of 2-acetoxy-3-chloro naphthoquinones towards the 1,3-dioxy diene (2) and the 1,1,3-trioxy diene (9) was examined. The competing influence of the acetoxy and chloro substituents was assessed from the regiochemistry of the resulting Diels–Alder chemistry, as was competition between that process and Michael addition/elimination. Reaction of the same dienes towards the less reactive 2,3-diacetoxy naphthoquinone (25) was also investigated.

Lactams as Hetero-Dienophiles in Diels-Alder Chemistry

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLactams as Hetero-Dienophiles in Diels-Alder ChemistryAndrew P. Degnan, Chong S. Kim, Charles W. Stout, and Aristotle G. KalivretenosCite this: J. Org. Chem. 1995, 60, 24, 7724–7725Publication Date (Print):December 1, 1995Publication History Published online1 May 2002Published inissue 1 December 1995https://doi.org/10.1021/jo00129a008RIGHTS & PERMISSIONSArticle Views225Altmetric-Citations9LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (259 KB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information Get e-Alerts

Approaches to carbocyclic analogues of the potent neuraminidase inhibitor 4-guanidino-Neu5Ac2en. X-Ray molecular structure of N-[(1S,2S,6R)-2-azido-6-benzyloxymethyl-4-formylcyclohex-3-enyl]acetamide

Various approaches using Diels–Alder chemistry have been established for the synthesis of truncated carbocyclic analogues 4 and 6 of 4-guanidino-Neu5Ac2en. In the case of compound 4, elaboration of an initial adduct from Danishefsky's diene and the dienophile 7 allowed access to the key enone 26. Methylenation of the carbonyl group and azide-induced opening of an intermediate oxazoline established the required framework regio- and stereo-specifically. Compounds 4 and 6 were found to retain interesting levels of antiviral activity comparable to those shown by their oxygen-containing counterparts.

Electrospray MS studies of C 60 Diels-Alder chemistry: Characterization of a C 60 Adduct with the Danishefsky Diene

The Diels-Alder reaction of C 60 with a crown-ether substituted diene as well as 1-methoxy-3-(trimethylsiloxyl)-1,3-butadiene (the Danishefsky Diene) is reported. C 60 shows dienophile reactivity comparable to N-phenylmaleimide.

Diels-Alder Chemistry of a 2,4-Dioxygenated Furan

Abstract The preparation of a 2,4-dioxygenated furan, 1, is reported. Its Diels-Alder reactivity with dienophiles is detailed.

Bis(tert-butylsulfonyl)acetylene as a general synthetic equivalent of alkynes in diels-alder chemistry. I: highly selective reduction and alkylating monodesulfonylation of z-1,2-bis(tert-butylsulfonyl)ethenes

Bicyclic (Z)-1,2-Bis(tert-butylsulfonyl)ethenes arising from Diels-Alder reactions of bis(tert-butylsulfonyl)acetylene are efficiently reduced to monosulfones by samarium(II) iodide and alkylatively monodesulfonylated by organolithium compounds.

Bis( tert-butylsulfonyl)acetylene as a general synthetic equivalent of alkynes in diels-alder chemistry. II: reductive and alkylative desulfonylations of bicyclic 1-alkyl-2-( tert-butylsulfonyl)ethenes

Both reductive and alkylative desulfonylations of bicyclic vinyl sulfones derived from Diels-Alder cycloadducts of bis( tert -butylsulfonyl)acetylene ( 1) are described. These transformations establish the synthetic equivalence of 1 with acetylene, 1-alkynes and internal alkynes in Diels-Alder chemistry.

Octahydroquinoline synthesis via immonium ion based Diels-Alder chemistry. Synthesis of (-)-8a-epipumiliotoxin C

Par addition intramoleculaire du methyl-5 dodecadiene-6,8ylidene ammonium (prepare a partir de l'aldehyde et de NH 4 Cl), synthese de 2 isomeres de methyl-5 octahydro-1,2,4a,5,6,7,8,8a propyl-2 quinoleine; reduction de l'un d'eux en (−)-epi-8a pumiliotoxine C

Metallic nickel-assisted room-temperature generation and Diels-Alder chemistry of o-xylylene intermediates

Metallic nickel-assisted room-temperature generation and Diels-Alder chemistry of o-xylylene intermediates

ChemInform Abstract: Applications of N‐Sulfinyl Dienophile Diels‐Alder Cycloadditions to Synthesis of Unusual Amino Sugars

The amino sugar moieties of staurosporine and nogalarol have been stereospecifically synthesized by a strategy utilizing N-sulfinyl Diels-Alder chemistry.

Total synthesis of a proposed structure of isohimachalone

A proposed structure 5 of the naturally occurring sesquiterpene ketone isohimachalone has been synthesized by a route using the unique Diels–Alder chemistry developed in our laboratory. The product has been shown to be non-identical with the natural material by comparison of spectral data, a result which has been implied by the work of an independent group using direct methods. Spectroscopic differences between our synthetic material and the natural and closely related products are discussed.

ChemInform Abstract: Synthesis of Spiro‐Compounds Related to Fredericamycin A.

Spiro-compounds [e.g., (8), (13)] that resemble the four central rings of the antitumour agent fredericamycin A have been synthesized by methods that are based on (i) intramolecular acylation and high-pressure Diels–Alder chemistry [(5)→(8)] or (ii) radical spiro-cyclization [e.g., (11)→(13)].

Synthesis of spiro-compounds related to fredericamycin A

Spiro-compounds [e.g., (8), (13)] that resemble the four central rings of the antitumour agent fredericamycin A have been synthesized by methods that are based on (i) intramolecular acylation and high-pressure Diels–Alder chemistry [(5)→(8)] or (ii) radical spiro-cyclization [e.g., (11)→(13)].

Aqueous intermolecular Diels-Alder chemistry: vernolepin revisited

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAqueous intermolecular Diels-Alder chemistry: vernolepin revisitedKiyoshi Yoshida and Paul A. GriecoCite this: J. Org. Chem. 1984, 49, 26, 5257–5260Publication Date (Print):December 1, 1984Publication History Published online1 May 2002Published inissue 1 December 1984https://doi.org/10.1021/jo00200a051RIGHTS & PERMISSIONSArticle Views391Altmetric-Citations29LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (585 KB) Get e-Alerts Get e-Alerts

Aqueous intermolecular Diels-Alder chemistry: reactions of diene carboxylates with dienophiles in water at ambient temperature

On prepare divers adduits monocycliques et bicycliques de Diels Alder par reaction de l'hexadiene-3,5 oate, et de l'heptadiene-4,6 oate de sodium avec divers dienophiles (benzoquinone, acroleine...) a temperature ambiante

Aqueous intermolecular diels-alder chemistry: novel products derived from substituted benzoquinone-diene carboxylate adducts via tandem Michael reactions

The aqueous intermolecular Diels-Alder reactions between 2,6- and 2,5-dimethylbenzoquinone and sodium ( E )-4,6-heptadienoate proceed in the presence of a catalytic amount of base to give rise via tandem Michael reactions to pentacyclic adducts 5 and 6 , respectively.

Liquid phase thermochemical energy conversion systems—An application of Diels-Alder chemistry

Thermochemical energy conversion at moderate or low temperature (> about 400°C) employing liquid phase components throughout a cycle is suggested as a promising concept for high-efficiency conversion of various energy sources (e.g. solar or industrial waste heat) to a convenient chemical form. In particular, we propose liquid phase Diels-Alder cycloaddition chemistry as an important class of reversible reactions for such low or moderate temperature thermochemical energy conversion systems. One of the important attributes of thermally driven Diels-Alder reactions is their concerted mechanism, with consequent high yields and efficiencies relative to liquid photochemical systems. Since the systems we propose involve organic species, with thermal stability concerns above about 400°C, it is important to demonstrate equilibrium shift capability for the highly energetic reactions sought. We have therefore carried out experimental studies with model liquid Diels-Alder systems that clearly demonstrate the degree of control over equilibrium available through substituent entropy effects. For example, Keq is unity at about 420°C (T*) for the anthracene/maleic anhydride system (in solvent) while a phenyl substituent on the anthracene or isopropyl substituent on the anhydride reduce T* to about 200°C at constant ΔH0. These results are of importance as regards subsequent systematic identification of Diels-Alder reactions having ideal thermochemical and physical properties. We also have developed a rapid NMR technique for qualitative screening of candidate reactions, and have applied this technique to the study of various bicyclic diene/fumaric acid ester systems. Our paper further points to the need for better understanding of the catalysis likely required for these liquid phase Diels-Alder reactions.

The diels-alder chemistry of 1-vinyl-2-pyridones

The Diels-Alder chemistry of a series of 1-vinyl-2-pyridones using a variety of dienophilic species including dimethyl acetylenedicarboxylate, benzyne, maleic anhydride and methyl vinyl ketone has been explored in order to determine the generality of this method for generation of N-vinylisoquinuclidines. In general, the cycloaddition reactions lead to modestly high yeilds of the azabicyclooctane products. In the course of these studies, we noted that retro-Diels-Alder reactions of N-vinylisoquinuclidienones lead to generation of N-vinylisocyanates and a benzene fragment while the corresponding mono-unsaturated isoquinuclidenones form the corresponding pyridones by elimination of an ethylene unit. Lastly, the regio- and stereochemical courses for the π2+ π4 addition reactions of methyl vinyl ketone and 1-vinyl-2-pyridones were investigated. The major products from these reactions appear to result from reaction pathways predicted to be of low energy using first-order molecular orbital methods.

You know the potential of Diels-Alder chemistry

You know the potential of Diels-Alder chemistry

You know the potential of Diels-Alder chemistry

You know the potential of Diels-Alder chemistry