3471-32-7Relevant articles and documents
Synthesis, structure and supramolecular properties of 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane
Liu, Bao-Yong,Zhang, Bin,Yang, Xi
, p. 1339 - 1341 (2015)
A new pyrazole derivative, 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane with m.f. C24H24N4O5 has been synthesized and the crystal structure was determined by single crystal X-ray diffraction. Interestingly, the title compound are linked by intermolecular O2-H22?N2 hydrogen bonds into a 36 atoms' macro-ring which is further held together into one dimensional beaded chain via C-H?O hydrogen bonding between another phenol oxygen atom and one methylene carbon atom.
Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine
Borate, Kailaskumar,Choi, Kyoungmin,Goetz, Roland,Hartwig, John F.,Shinde, Harish,Wang, Justin Y.,Zuend, Stephan J.
supporting information, p. 399 - 408 (2020/10/29)
Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.
One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis
Akporji, Nnamdi,Braga, Felipe C.,Gabriel, Christopher M.,Landstrom, Evan B.,Lee, Nicholas R.,Lipshutz, Bruce H.
supporting information, (2020/09/02)
An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.
