14959-65-0Relevant academic research and scientific papers
Construction of isoquinolin-1(2H)-ones by copper-catalyzed tandem reactions of 2-(1-Alkynyl)benzaldimines with water
Zhang, Mingliang,Zhang, Hui-Jun,Ruan, Wenqing,Wen, Ting-Bin
supporting information, p. 5914 - 5918 (2015/09/22)
The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl)benzaldimines to give the corresponding isoquinolinium intermediates. The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones is developed. 4-Halogen-substituted isoquinolin-1(2H)-ones can be obtained in good yields simply by including N-halosuccinimides (NXS) in the reaction system. Mechanistic studies are also undertaken.
A simple access to N-(un)substituted isoquinolin-1(2H)-ones: Unusual formation of regioisomeric isoquinolin-1(4H)-ones
Chary, R. Gangadhara,Dhananjaya,Prasad, K. Vara,Vaishaly,Ganesh,Dulla, Balakrishna,Kumar, K. Shiva,Pal, Manojit
, p. 6797 - 6800 (2014/06/23)
A ligand/additive/Pd-free Cu-mediated coupling/cyclization strategy afforded the first practical, one-pot and general approach towards synthesis of N-(un)substituted isoquinolin-1(2H)-ones. Both the catalyst and the solvent used are recyclable. The use of the Cu reagent in excess led to the unusual formation of regioisomeric and uncommon isoquinolin-1(4H)-ones. This journal is the Partner Organisations 2014.
Transition metal-free cascade reactions of alkynols to afford isoquinolin-1(2H)-one and dihydroisobenzofuran derivatives
Li, Deng Yuan,Shi, Ke Ji,Mao, Xiao Feng,Chen, Guo Rong,Liu, Pei Nian
, p. 4602 - 4614 (2014/06/09)
Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
Solvent-switched benzylic methylene functionalization: Addition, ring-opening, cyclization, and unexpected cleavage of C-O and C-C bonds
Li, Deng Yuan,Shang, Xue Song,Chen, Guo Rong,Liu, Pei Nian
supporting information, p. 3848 - 3851 (2013/09/02)
Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition
Synthesis of heterocycles with MF/Al2O3 base-systems: 2-arylbenzofuranes and 2,3-diarylisoquinolin-1(2H)-ones
Hellwinkel,Goke
, p. 1135 - 1141 (2007/10/02)
2-Benzyloxybenzaldehydes, -acetophenones and -benzophenones substituted in the benzyl part with electron-withdrawing groups, cyclize easily to 2-arylbenzofuranes by using a standardized KF- or CsF-Al2O3 base system. An efficient one-pot synthesis for 2,3-diarylisoquinolin-1(2H)-ones is possible by reacting a variety of arene carbaldehyde anils with phthalides under the same reaction conditions.
