Author
Jean-Paul Pradère
Other affiliations: Centre national de la recherche scientifique
Bio: Jean-Paul Pradère is an academic researcher from University of Nantes. The author has contributed to research in topics: Cycloaddition & Thiazine. The author has an hindex of 9, co-authored 36 publications receiving 267 citations. Previous affiliations of Jean-Paul Pradère include Centre national de la recherche scientifique.
Topics: Cycloaddition, Thiazine, Reactivity (chemistry), Diene, Chiral auxiliary
Papers
More filters
TL;DR: Pyridazine C-nucleosides have been synthesized by [4+2] cycloaddition of alkynyl C nucleoside with substituted tetrazines as mentioned in this paper.
31 citations
TL;DR: Magnesium bromide mediated hetero Diels-Alder cycloaddition of diene 1 (R 1 = Ph) to chiral N-acryloyl-2-oxazolidinone 4b leads to 5b as the sole adduct formed as discussed by the authors.
Abstract: Magnesium bromide mediated hetero Diels-Alder cycloaddition of diene 1 (R 1 = Ph) to chiral N-acryloyl-2-oxazolidinone 4b leads to 5b as the sole adduct formed. Chiral auxiliary removal leads to enantiomerically pure 5,6-dihydro-4H- 1,3-thiazine 3 (R 2 = Bn). The selectivity of the cycloaddition is reversed under thermal or high pressure activation. The predominant diastereomeric adduct 6b is isolated in pure form after flash chromatography. For some years, studies in our laboratory have focused on the construction of the dihydro-l,3-thiazine ring, a subunit found in biologically active natural products (eg. cepharnycin C) as well as in many unnatural compounds displaying a broad range of activities (medicinal drugs, herbicids, pesticids, etc). In particular it has been shown that the hetero Diels-Alder reaction of 3-aza-4-dimethylamino-l-thia-butadienes I with acrylates 2 induced by heating 1 or by application of high pressure 2 provides a convenient and efficient route to substituted 5,6-dihydro-4H-1,3-thiazines 3, allowing for the simultaneous construction of carbon-carbon and sulfur-carbon bonds and installation of two contiguous stereogenic centers (Scheme 1).
29 citations
TL;DR: The cycloaddition of 2- or 2,3-substituted 1-thia- and 1 -thia-3-aza-4-dimethylamino-buta-1, 3-dienes with various dienophiles in the presence of a Lewis acid provides a rapid and diastereoselective access to the 3,4-dihydro-2H-thiopyran and 5,6-diphysine backbones as discussed by the authors.
21 citations
TL;DR: In this article, the behaviour of endo selective diene 4 in kinetically controlled hetero Diels-Alder cycloadditions was studied in the context of aza analogue.
21 citations
TL;DR: The bielectronic electrochemical reduction of pyridazines, substituted by electron-withdrawing groups, leads to their corresponding 1,2-dihydro derivatives as mentioned in this paper.
18 citations
Cited by
More filters
TL;DR: This review discusses advances in synthetic organic electrochemistry since 2000 with enabling methods and synthetic applications analyzed alongside innate advantages as well as future challenges of electroorganic chemistry.
Abstract: Electrochemistry represents one of the most intimate ways of interacting with molecules. This review discusses advances in synthetic organic electrochemistry since 2000. Enabling methods and synthetic applications are analyzed alongside innate advantages as well as future challenges of electroorganic chemistry.
1,930 citations
1,378 citations
338 citations
TL;DR: In this article, an overview is given for the period since 1989 describing the reaction of heterobutadienes and other dienophiles such as carbonyls, thiocarbonyls and iminium salts.
Abstract: The hetero Diels-Alder reaction is one of the most important methods for the synthesis of heterocycles. In this article an overview is given for the period since 1989 describing the reaction of heterobutadienes such as oxabutadienes, thiabutadienes, azabutadienes, diaazabutadienes, nitroso-alkenes and nitroalkenes as well as of heterodienophiles such as carbonyls, thiocarbonyls, imines, iminium salts, azo- and nitroso compounds. In addition, several other less common hetero Diels-Alder reactions such as cycloadditions of thiaazabutadienes, oxaazabutadienes, dioxabutadienes, dithiabutadienes, oxathiabutadienes, diazaoxabutadienes as well as the use of N-sulfinyl-phosphaalkynes and other dienophiles are mentioned. A main point of discussion is the stereoselectivity of the reactions and the preparation of enantiopure compounds either using dienes and dienophiles carrying a chiral auxiliary or employing chiral Lewis acids. A point stressed is the synthesis of natural products using hetero Diels-Alder reactions leading to carbohydrates, alkaloids, terpenes, antibiotics, mycotoxins, cytochalasans, antitumor agents and several other classes of natural products.
317 citations
TL;DR: While natural and synthetic N-nucleosides are vulnerable to enzymatic and acid-catalyzed hydrolysis of the nucleosidic bond, their C-analogues are much more stable and have found numerous applications in medicinal chemistry and chemical biology.
Abstract: While natural and synthetic N-nucleosides are vulnerable to enzymatic and acid-catalyzed hydrolysis of the nucleosidic bond, their C-analogues are much more stable. Several C-nucleosides are naturally occurring compounds, e.g., pseudouridine (isolated from the yeast t-RNA) and showdomycin (an antibiotic). Development of novel synthetic methodologies allowed the preparation of a large variety of synthetic analogues, which found numerous applications in medicinal chemistry and chemical biology. Most important biologically active C-nucleosides are the inhibitors of purine nucleosides phosphorylase or IMP dehydrogenase. A number of artificial aryl-C-nucleosides capable of π-stacking are being vigorously investigated as building blocks in chemical biology. In the past few years, several Artificial Expanded Genetic Information Systems (AEGIS)1 have been successfully developed as prime examples of synthetic biology, a newly emerging interdisciplinary area, with the ultimate goal to design systems where high-level behaviors of the living matter are mimicked by artificial chemical systems.2,3
269 citations