The reaction of 2-(diphenylmethylene)thietan-3-one (2) with 1,2,4,5-tetrazines (3a-c) in KOH/MeOH/THF gives 4H-pyrazolo[5,1-c]thiazines (7a-c). This no vel condensation reaction proceeds via the intermediacy of an 8-(diphenylmethylene)-2H-1,4,5-thiadiazocin-7(8H)-one (5), which undergoes a multi-step rearrangement including a rare anti-Michael addition.
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http://dx.doi.org/10.1016/j.tetlet.2006.09.015 | DOI Listing |
Chem Asian J
October 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Transit Campus, Govt. ITI Building, NH 59, Engineering School Road, Ganjam-District, Berhampur, 760 010, Odisha, India.
Synthesis of functionalized 1,3-indandiones containing-cyclopentenones and -benzotropones has been achieved by the reaction of 1,5-diphenylpenta-1,4-diyn-3-ones with 1,3-indandiones, bindone respectively. The developed method involves Michael-anti-Michael addition cascade reactions under transition-metal-free conditions. This is the first report to synthesise diverse benzotropone fused with 1,3-indandiones under transition metal-free conditions from bindone.
View Article and Find Full Text PDFOrg Lett
August 2024
Department of Applied Chemistry, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
Here we report a palladium-catalyzed -Michael-type hydroamination of -(quinolin-8-yl)acrylamide with 2-pyridones. The use of a palladium catalyst enables the α-addition of 2-pyridones, resulting in the formation of a range of -substituted 2-pyridone carboxamides with yields ranging from 10% to 80%. Derivatization of the products highlights the utility of this transformation.
View Article and Find Full Text PDFJ Am Chem Soc
May 2024
Department of Applied Chemistry, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
This paper reports a direct α-(hetero)arylation of acrylamides through an inverse electron-demand nucleophilic addition, specifically an -Michael-type addition. The introduction of a quinolyl directing group facilitates the nucleophilic addition of (hetero)arenes to the α-position of acrylamides. The quinolyl directing group effectively suppresses undesired β-hydrogen elimination and is removable for subsequent derivatization.
View Article and Find Full Text PDFJ Org Chem
April 2022
Equipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS, UMR 7177, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg, France.
-Allenamides, substituted by an ester at the γ-position, were obtained through addition of terminal ynamides with ethyl diazoacetate under copper catalysis for the first time. Regio- and stereoselective hydroamination of those activated -allenamides provided exclusively -configured captodative enamimes through a one-pot anti-Michael addition. Numerous ynamides as well as various secondary amines were adapted in this process.
View Article and Find Full Text PDFJ Org Chem
January 2022
School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
An efficient protocol involving the transformation of sequentially generated recursive anions from heterocyclic precursors to orthogonally strap diynones through one pot transition-metal-free spirocyclopentannulation has been devised, employing oxindoles and pyrazolones as prototypical platforms. Insights into these regioselective tandem Michael--Michael processes have been gleaned through DFT calculations.
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