Journal ArticleDOI
Expeditious synthesis of new 1,2,3-thiadiazoles and 1,2,3-selenadiazoles from 1,2-diaza-1,3-butadienes via Hurd-Mori-type reactions.
Orazio A. Attanasi,Lucia De Crescentini,Gianfranco Favi,P. Filippone,Gianluca Giorgi,F. Mantellini,Stefania Santeusanio +6 more
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TLDR
Alpha-substituted hydrazones obtained from 1,2-diaza-1,3-butadienes and methylenic or methinic activated substrates gave rise to a wide range of cyclic compounds.Abstract:
α-Substituted hydrazones obtained from 1,2-diaza-1,3-butadienes and methylenic or methinic activated substrates gave rise to a wide range of cyclic compounds. In particular, in the presence of thionyl chloride as solvent-reagent, they were transformed into 1,2,3-thiadiazoles,1 with selenium oxychloride in new 4-substituted 2,3-dihydro-1,2,3-selenadiazoles, while with selenium dioxide, they were transformed into 4-substituted 1,2,3-selenadiazoles. We have also examined the nucleophilic behavior of 1,2,3-thiadiazole 4a in the reaction with 1,2-diaza-1,3-butadienes that produced, under basic conditions, 4-hydrazono-1-(1,2,3-thiadiazolyl)pentane derivatives. This event represents an interesting example of stereoselective synthesis because it leads exclusively to the formation of the RR/SS racemic mixture. These latter compounds, treated with thionyl chloride, gave the corresponding 1,3-di-1,2,3-thiadiazolylpropane derivatives, while with sodium methoxide they afforded 1,2,3-thiadiazolyl-2-oxo-2,3-dihydro-1H-p...read more
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Cultivating the Passion to Build Heterocycles from 1,2‐Diaza‐1,3‐dienes: the Force of Imagination
Orazio A. Attanasi,Lucia De Crescentini,Gianfranco Favi,Paolino Filippone,Fabio Mantellini,Francesca R. Perrulli,Stefania Santeusanio +6 more
TL;DR: In this article, the main target of the microreview is to outline some of the reactive peculiarities that make 1,2-diaza-1,3-dienes reactive.
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Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles†
Zhijin Fan,Zhikun Yang,Haike Zhang,Na Mi,Huan Wang,Fei Cai,Xiang Zuo,Qingxiang Zheng,Hai-Bin Song +8 more
TL;DR: Fungicide screening indicated that all of the target compounds showed certain extent of growth inhibition against fungi tested and potential fungicide lead compounds were found to have potential wide spectrum of fungicide activity.
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1,2,3-Selenadiazole thioacetanilides: synthesis and anti-HIV activity evaluation.
TL;DR: Novel series of 1,2,3-selenadiazole thioacetanilide derivatives were designed, synthesized using an original synthetic route, structurally confirmed by spectral analysis, and evaluated for their anti-HIV activity in MT-4 cells, showing that only compound 7f possessed potent activity against HIV-1 replication.
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Lewis Acid/Rhodium-Catalyzed Formal [3 + 3]-Cycloaddition of Enoldiazoacetates with Donor-Acceptor Cyclopropanes
TL;DR: A formal [3 + 3]-cycloaddition of enoldiazoacetates with donor-acceptor cyclopropanes was realized by the combination of a Lewis acid-catalyzed diastereoselective cycle and a subsequent rhodium-Catalyzed chemoselectives ring expansion.
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Cycloaddition Reactions of Phosphorylated 1,2‐Diaza‐1,3‐butadienes with Olefins: Regioselective Synthesis of Pyridazine Derivatives
TL;DR: In this paper, the aza-Diels-Alder reaction of 4-phosphinyl- and 4phosphonyl-1,2-diaza-1-3-butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported.
References
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Estrogenic Activities of 517 Chemicals by Yeast Two-Hybrid Assay
Tsutomu Nishihara,Jun-ichi Nishikawa,Tomohiko Kanayama,Fumi Dakeyama,Koichi Saito,Masayoshi Imagawa,Satoshi Takatori,Yoko Kitagawa,Shinjiro Hori,Hideo Utsumi +9 more
TL;DR: A simple and rapid screening method using the yeast two-hybrid system based on the ligand-dependent interaction of nuclear hormone receptors with coactivators to test the estrogenic activity of chemicals.
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A novel synthesis of selenium heterocycles: substituted 1,2,3-selenadiazoles
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Synthesis and platelet aggregation inhibitory activity of 4,5-bis(substituted)-1,2,3-thiadiazoles
TL;DR: In order to develop a structure-activity relationship for this heterocycle, a number of new 4(5)-mono- and -disubstituted 1,2,3-thiadiazoles were synthesized and the most active compounds were those in which the heterocycles was substituted with benzene rings possessing para electron-donating groups.
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