TY - JOUR
T1 - Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion
AU - Collet, Jurriën W.
AU - Van Der Nol, Edith A.
AU - Roose, Tom R.
AU - Maes, Bert U.W.
AU - Ruijter, Eelco
AU - Orru, Romano V.A.
PY - 2020/6/5
Y1 - 2020/6/5
N2 - Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.
AB - Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.
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U2 - 10.1021/acs.joc.0c00771
DO - 10.1021/acs.joc.0c00771
M3 - Article
AN - SCOPUS:85087356600
VL - 85
SP - 7378
EP - 7385
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 11
ER -
