29637-85-2Relevant academic research and scientific papers
Aza-Diels-Alder reactions and synthetic applications of thio-substituted 1,3-dienes with arylsulfonyl isocyanates
Chou,Hung
, p. 8323 - 8326 (2000)
The first aza-Diels-Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of regio- and chemoselectivity. The cyclized products 3a and 4 underwent further interesting reactions with nucleophiles and bases to give useful heterocyclic compounds. (C) 2000 Elsevier Science Ltd.
Iron-Catalyzed Reactions of 2-Pyridone Derivatives: 1,6-Addition and Formal Ring Opening/Cross Coupling
Huang, Lin,Gu, Yiting,Fürstner, Alois
supporting information, p. 4017 - 4023 (2019/08/07)
In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.
Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins
Gogsig, Thomas M.,Lindhardt, Anders T.,Dekhane, Mouloud,Grouleff, Julie,Skrydstrup, Troels
supporting information; experimental part, p. 5950 - 5955 (2010/02/28)
Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete aregioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized α-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.
Synthesis and applications of tetrahydro-2-pyridinones via aza-Diels - Alder reactions of thio-substituted 1,3-dienes with arylsulfonyl isocyanates
Chou,Hung
, p. 2450 - 2462 (2007/10/03)
The first aza-Diels - Alder reactions of arylsulfonyl isocyanates with thio-substituted 1,3-dienes via the 3-sulfolene precursors 1 gave the cyclized products 3 with complete control of chemo- and regioselectivity. The cyclized products 3a and 5 underwent further reactions with nucleophiles and bases to give useful heterocyclic compounds. The N-tosyl group of the cyclic products could be selectively replaced by hydrogen or another substituent.
