129849-05-4Relevant articles and documents
One-pot synthesis of 4-methylisoquinolines via a sequential Pd-catalyzed Heck reaction and intramolecular cyclization
Tian, Yulin,Qi, Jianguo,Sun, Chenbin,Yin, Dali,Wang, Xiaojian,Xiao, Qiong
supporting information, p. 7262 - 7266 (2013/10/22)
An efficient, one-pot synthesis of 4-methylisoquinolines via a cascade Pd-catalyzed Heck reaction, intramolecular cyclization and isomerization has been developed. This reaction has a wide range of substrates with various functional groups, and the corresponding products have been obtained in good yields.
3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators
Ortar, Giorgio,Schiano Moriello, Aniello,Morera, Enrico,Nalli, Marianna,Di Marzo, Vincenzo,De Petrocellis, Luciano
, p. 5614 - 5618 (2013/10/01)
Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylidenephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds.
Synthesis of isoindole derivatives by palladium-catalyzed domino reaction of (2-alkynyl)phenylketone o-pentafluorobenzoyloximes
Kitamura, Mitsuru,Moriyasu, Yohei,Okauchi, Tatsuo
experimental part, p. 643 - 646 (2011/05/02)
Isoindole derivatives were synthesized by the palladium-catalyzed cyclization of (2-alkynyl)phenylketone O-pentafluoro-benzoyloximes in the presence of organometallic compounds such as sodium formate and aryl boronic acid. Georg Thieme Verlag Stuttgart - New York.
Formal aromatic C-H insertion for stereoselective isoquinolinone synthesis and studies on mechanistic insights into the C-C bond formation
Park, Chan Pil,Nagle, Advait,Cheol, Hwan Yoon,Chen, Chiliu,Kyung, Woon Jung
supporting information; experimental part, p. 6231 - 6236 (2009/12/08)
(Chemical Equation Presented) Formal aromatic C-H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C-H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by substituent effects on the aromatic ring and a secondary deuterium kinetic isotope effect. Various isoquinolinones were synthesized intramolecularly via six-membered ring formation with high regioand diastereoselectivity, while averting the common Buchner-type reaction. Intermolecularly, dirhodium catalyzed formal aromatic C-H insertion on electron-rich aromatics was also achieved.
Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
Seganish, W. Michael,DeShong, Philip
, p. 1137 - 1143 (2007/10/03)
Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
, p. 9964 - 9970 (2007/10/03)
Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
A new synthesis of 3-ylidenephthalides via palladium-catalyzed cyclocarbonylation of 2-triflyloxyacetophenones
Ciattini,Mastropietro,Morera,Ortar
, p. 3763 - 3766 (2007/10/02)
The reaction of 2-triflyloxyacetophenone derivatives 1 with carbon monoxide in the presence of a palladium catalyst affords 3-ylidenephthalides 2 in good yields and under mild conditions.
Palladium Catalysis in Cephalosporin Chemistry: General Methodology for the Synthesis of Cephem Side Chains
Farina, Vittorio,Baker, Stephen R.,Benigni, Daniel A.,Hauck, Sheila I.,Sapino, Chester
, p. 5833 - 5847 (2007/10/02)
We describe in full the palladium-catalyzed coupling of 3-(triflyloxy)cephems with organotin compounds, leading to the synthesis of 3-alkenyl-, 3-alkynyl-, and 3-arylcephems under exceptionally mild conditions.While this approach was not satisfactory for
