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Majid Ghazanfarpur-Darjani

Bio: Majid Ghazanfarpur-Darjani is an academic researcher from Tarbiat Modares University. The author has contributed to research in topics: Sulfonyl. The author has an hindex of 2, co-authored 2 publications receiving 30 citations.
Topics: Sulfonyl

Papers
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Journal ArticleDOI
TL;DR: In this paper, a copper-catalyzed synthesis of N-sulfonylamidines via three-component coupling of sulfonyl azides, terminal alkynes, and trialkylamines is reported.

30 citations

Journal ArticleDOI
TL;DR: The three-component reaction involves coupling of copper acetylides with azides to give ketimine intermediates which are trapped by trialkylamines to yield the title compounds as mentioned in this paper.
Abstract: The three-component reaction involves coupling of copper acetylides with azides to give ketimine intermediates which are trapped by trialkylamines to yield the title compounds.

2 citations


Cited by
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Journal ArticleDOI
TL;DR: The review of several practical and versatile approaches to ketenimine chemistry and the discovery of a variety of highly efficient reactions are presented here.
Abstract: Ketenimines are an important class of reactive species and useful synthetic intermediates. During the last two decades several practical and versatile approaches to ketenimines have been developed, leading to exhaustive investigations on ketenimine chemistry and the discovery of a variety of highly efficient reactions. Five types of reactions for ketenimines have been reported, including nucleophilic additions (ketenimines can be used as both electrophiles and nucleophiles), radical additions, cycloaddition reactions, electrocyclic ring closure reactions, and σ rearrangements. Furthermore, numerous complex organic compounds, particularly the biologically interesting heterocycles, have been constructed using these methodologies. The review of these accomplishments is presented here.

207 citations

Journal ArticleDOI
TL;DR: A detailed study of amidine synthesis from N-allyl-N-sulfonyl ynamides is described here, and another set of tandem sigmatropic rearrangements are uncovered, leading to vinyl imidate formation.
Abstract: A detailed study of amidine synthesis from N-allyl-N-sulfonyl ynamides is described here. Mechanistically, this is a fascinating reaction consisting of diverging pathways that could lead to deallylation or allyl transfer depending upon the oxidation state of palladium catalysts, the nucleophilicity of amines, and the nature of the ligands. It essentially constitutes a Pd(0)-catalyzed aza-Claisen rearrangement of N-allyl ynamides, which can also be accomplished thermally. An observation of N-to-C 1,3-sulfonyl shift was made when examining these aza-Claisen rearrangements thermally. This represents a useful approach to nitrile synthesis. While attempts to render this 1,3-sulfonyl shift stereoselective failed, we uncovered another set of tandem sigmatropic rearrangements, leading to vinyl imidate formation. Collectively, this work showcases the rich array of chemistry one can discover using these ynamides.

73 citations

Journal ArticleDOI
TL;DR: A comprehensive review of the evolution and growing importance of this merge of two vibrant concepts in modern organic synthesis can be found in this article, where the authors provide a comprehensive examination of selected works that highlight the evolution of the merge of sustainable metal catalysis and C H activation.

72 citations

Journal ArticleDOI
TL;DR: Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amine, followed by hydroamidation of the ynamine intermediate with the sulfonamide.
Abstract: Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu(OTf)2 (5 mol %) produces amidines selectively without Glaser–Hay alkyne homocoupling products. Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amine, followed by hydroamidation of the ynamine intermediate with the sulfonamide.

50 citations

Journal ArticleDOI
TL;DR: A novel and efficient one-pot method for the synthesis of cyclopropane-fused bicyclic amidines on the basis of a CuBr2 -mediated oxidative cyclization of carbanions that provides straightforward access to biologically active and pharmaceutically important 3-azabicyclo[n.1.0]alkane frameworks under mild conditions.
Abstract: A novel and efficient one-pot method has been developed for the synthesis of cyclopropane-fused bicyclic amidines on the basis of a CuBr2 -mediated oxidative cyclization of carbanions. The usefulness of this unique multicomponent strategy has been demonstrated by the use of a wide variety of substrates to furnish novel cyclopropane-containing amidines with a quaternary center in very good yields. This ketenimine-based approach provides straightforward access to biologically active and pharmaceutically important 3-azabicyclo[n.1.0]alkane frameworks under mild conditions. The synthetic power of this methodology is exemplified in the concise synthesis of the pharmaceutically important antidepressant drug candidate GSK1360707 and key intermediates for the synthesis of amitifadine, bicifadine, and narlaprevir.

34 citations