1402611-35-1Relevant articles and documents
Flow reactor approach for the facile and continuous synthesis of efficient Pd@Pt core-shell nanoparticles for acceptorless dehydrogenative synthesis of pyrimidines from alcohols and amidines
Poly, Sharmin Sultana,Hashiguchi, Yuta,Sultana, Asima,Nakamura, Isao,Shimizu, Ken-ichi,Yasumura, Shunsaku,Fujitani, Tadahiro
, (2021/04/23)
Carbon supported Pd@Pt core-shell nanoparticles catalyst was prepared in a flow reactor toachieve enhanced catalytic activities with low Pt loading for the acceptorless dehydrogenative synthesis of pyrimidines. Spectroscopic (XAS analysis) and microscopic (HAADF-STEM) techniques reveled that the core-shell structure was formed by the applied preparation method. The Pd@Pt/PVP (polyvinylpyrrolidone)/C catalyst showed the activity for the three component one pot synthesis of pyrimidines through a series of consecutive reactions including oxidation of alcohols, C[sbnd]C, and C[sbnd]N coupling, followed by heterocyclization and dehydrogenation employing various primary alcohols, secondary alcohols, and amidines. The reaction mechanism on Pd@Pt/PVP/C catalyst was explored by comparison with the control experiments.
Acceptorless Dehydrogenative Synthesis of Pyrimidines from Alcohols and Amidines Catalyzed by Supported Platinum Nanoparticles
Sultana Poly, Sharmin,Siddiki, S. M. A. Hakim,Touchy, Abeda S.,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Kanda, Yasuharu,Shimizu, Ken-Ichi
, p. 11330 - 11341 (2019/01/03)
A one-pot, acceptorless dehydrogenative method, using a carbon-supported Pt catalyst (Pt/C) along with KOtBu, has been developed for the synthesis of 2,4,6-trisubstituted pyrimidines from secondary and primary alcohols, and amidines. The reaction takes place efficiently using a wide range of substrate scopes (32 examples with isolated yields up to 92%). The Pt/C catalyst that promotes this process is reusable and has a higher turnover number (TON) than those employed in previously reported methods. The results of mechanistic studies suggest that the process takes place through a pathway that begins with Pt-catalyzed acceptorless dehydrogenation of the alcohol substrate, which is followed by sequential condensation, cyclization, and dehydrogenation. Measurements of the turnover frequency combined with the results of density functional theory calculations on different metal surfaces suggest that the adsorption energy of H on the Pt surface is optimal for the acceptorless dehydrogenation process, which causes the higher catalytic activity of Pt over those of other metals.
Stereoselective and catalytic access to β-enaminones: An entry to pyrimidines
Gayon, Eric,Szymczyk, Monika,Gérard, Hélène,Vrancken, Emmanuel,Campagne, Jean-Marc
, p. 9205 - 9220 (2013/01/15)
We describe herein a highly stereoselective access to Cbz-protected β-enaminones 2 based on the NaOH catalyzed rearrangement of propargylic hydroxylamines 1. The synthetic potential of these β-enaminones is illustrated in an original synthesis of pyrimidi