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Synthesis and reactivity of 5-methylenehydantoins |
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| Authors: | José M Fraile Gustavo Lafuente José A Mayoral Antonio Pallarés |
| Institution: | a Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), C.S.I.C., Universidad de Zaragoza, Departamento de Química Orgánica, Pedro Cerbuna 12, E-50009 Zaragoza, Spain b Instituto Universitario de Catálisis Homogénea (IUCH), C.S.I.C., Universidad de Zaragoza, Departamento de Química Orgánica, Pedro Cerbuna 12, E-50009 Zaragoza, Spain c Deretil, E-04618 Villaricos (Almería), Spain |
| Abstract: | 5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group. |
| Keywords: | Hydantoins Conjugate additions Diels-Alder Epoxidation |
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