1600515-03-4Relevant academic research and scientific papers
One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
Xie, Jialin,Guo, Zhonglin,Huang, Yuanqiong,Qu, Yi,Song, Hongjian,Song, Haibin,Liu, Yuxiu,Wang, Qingmin
, p. 490 - 495 (2019)
An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int
Synthesis of 3-Keto Pyridines from the Conjugated Allenone – Alkynylamine Oxidative Cyclization Catalyzed by Supported Au Nanoparticles
Fragkiadakis, Michael,Kidonakis, Marios,Stratakis, Manolis,Zorba, Leandros
, p. 964 - 968 (2020/01/28)
Recyclable supported Au nanoparticles on TiO2 catalyze the cyclization of N-propargyl or N-homopropargyl β-enaminones followed by dehydrogenation (aromatization) leading to substituted 3-keto pyridines or 4-picolines in very good yields. This pathway is in contrast to their known cyclization in the presence of Au(I) or Au(III) catalysts which provides 1,4-oxazepines, instead. The enaminones are formed in situ upon mixing a conjugated allenone or allenyl ester with the alkynylamine, thus the pyridine-forming transformation is typically a one pot process. (Figure presented.).
Electrophile-Mediated Reactions of Functionalized Propargylic Substrates
Urbanaite, Aurelija,Jonu?is, Mantas,Buk?naitiene, Rita,Balkaitis, Simonas,?ikotiene, Inga
supporting information, p. 7091 - 7113 (2015/11/16)
Metal-free halogen, chalcogen, or oxocarbenium ion mediated yne-carbonyl or yne-thioxo transformations of a range of N- and O-propargylic compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4H-1,3-oxazines, 4H-1,3-thiazines, 4,5-dihydrothiazoles, and α-substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes. Metal-free electrophile-mediated transformations of various N- and O-propargylic compounds have been studied. The scope and limitations of these reactions have been evaluated by using a broad range of substrates.
Novel method of tetramic acid synthesis: Silver-catalyzed carbon dioxide incorporation into propargylic amine and intramolecular rearrangement
Ishida, Tomonobu,Kobayashi, Ryo,Yamada, Tohru
, p. 2430 - 2433 (2014/05/20)
Tetramic acid derivatives have been studied as biologically active heterocycle structures for pharmaceutical or agricultural chemicals. Conventional preparative approaches often require highly functionalized starting materials and harsh heating conditions in basic media. The present report provides a conceptually new synthetic strategy for the synthesis of tetramic acid derivatives from easily available propargylic amines and carbon dioxide with a silver salt and DBU under mild reaction conditions.
