Pd/C-catalyzed reductive formylation of indoles and quinolines using formic acid
A two-step, one-pot domino reaction methodology was developed to synthesize a variety of N-formylindolines and N-formyltetrahydroquinolines from the corresponding indoles and quinolines. In the first step, the heterocyclic compounds are reduced to the corresponding dihydro or tetrahydro products by a Pd/C-catalyzed transfer hydrogenation using formic acid as a hydrogen donor. In the second step, nitrogen is formylated by formic acid to afford the final products in very good isolated yields. Georg Thieme Verlag Stuttgart New York.
Kulkarni, Aditya,Gianatassio, Ryan,Toeroek, Bela
scheme or table
p. 1227 - 1232
(2011/05/14)
Radical ring closures of 4-isocyanato carbon-centered radicals
The 2-(2-isocyanatophenyl)ethyl radical was generated from the corresponding bromide with tributyltin and tris(trimethylsilyl)silyl radicals and shown to ring close in the 6-endo-mode to afford 3,4-dihydro-1H-quinolin-2-one as the major product. Cyclization in the 5-exo-mode to produce 2,3-dihydroindole-1-carbaldehyde, after hydrogen abstraction, was a minor reaction. Rate constants for the two processes were estimated and compared with reaction enthalpies computed by the DFT method.
Minin, Patricia L.,Walton, John C.
p. 2960 - 2963
(2007/10/03)
Catalytic Transfer Hydrogenation of Indoles to Indolines in Formic Acid
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Kikugawa, Yasuo,Kashimura, Masato
p. 785 - 787
(2007/10/02)
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