A small library of natural product-like compounds has been assembled by coupling an Ugi multicomponent reaction with two postcondensation transformations, carried out in one-pot fashion: a S(N)2' cyclization followed by an intramolecular Heck reaction.
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One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction.
Org Lett
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Engineering Research Center of Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan 030006, P. R. of China.
Herein a novel and robust methodology to spiroimidazolidinones has been developed under a mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids , aldehydes , amines , isocyanides , and isocyanides produced regioselectively spiroimidazolidinones in 71-88% yields via a sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation reaction. Furthermore, the easily accessible starting materials, high bond-forming efficiency, and broad substituent tolerance make this strategy useful in synthetic and medicinal chemistry.
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Sci Rep
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College of Management Science, Chengdu University of Technology, 1 East Third Road, Erxian Bridge, Chenghua District, Chengdu, 610059, Sichuan, P.R. China.
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Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, Mexico.
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