Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides
A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).
Formation of isoquinoline derivatives by the irradiation of N-acetyl-α-dehydrophenylalanine ethyl ester and its derivatives
The irradiation of a nitrogen-purged acetonitrile solution of the title compounds (1) with Pyrex filtered light was found to give isoquinoline derivatives (2) via the excited state (Z)-isomers, whereas in methanol 1-azetine derivative was also detected al
Ethyl α-amino-β,β-diethoxypropionate, a useful synthon for the preparation of 3,4-fused pyridine-6-carboxylates from aromatic aldehydes
An efficient synthesis of ethyl α-amino-β,β-diethoxypropionate (1), via a titanium tetrachloride-catalyzed coupling reaction of ethyl nitroacetate and triethyl orthoformate, is described. Condensation of 1 with various aldehydes followed by reduction and
Singh, Sunil K.,Dekhane, Mouloud,Le Hyaric, Mireille,Potier, Pierre,Dodd, Robert H.
p. 379 - 391
(2007/10/03)
Vinyl Azides in Heterocyclic Synthesis. Part 2. Selectivity in the Decomposition of Azidocinnamates with Olefinic ortho-Substituents
Thermolysis of azidocinnamates with an olefinic o-substituent gives products (isoquinolines, azepines, aziridines) formed by selective interaction of the azide, and the derived nitrene, with the olefinic substituent, cyclisation onto the unsubstituted aro
Hickey, Deirdre M. B.,Moody, Christopher J.,Rees, Charles W.
p. 1113 - 1118
(2007/10/02)
Selectivity in Vinyl Azide Reactions; Decomposition of Azidocinnamates with Olefinic ortho-Substituents
Thermal decomposition of vinyl azides (1a - c) gives isoquinolines (3), benzazepines (4), or aziridines (5) and (6) by preferential reaction at the unsaturated substituent; removal of this unsaturation as in the epoxides (1d, 1e) leads exclusively to 4-substituted indoles.
Hickey, Deirdre M. B.,Moody, Christopher J.,Rees, Charles W.
p. 1419 - 1421
(2007/10/02)
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