Continuous Synthesis of Hydantoins: Intensifying the Bucherer-Bergs Reaction

Autor(es)

Monteiro, Julia L. ^{[1, 2]} ; Pieber, Bartholomaeus ^[2] ; Correa, Arlene G. ^[1] ; Kappe, C. Oliver ^[2]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

^[2] Graz Univ, Inst Chem, NAWI Graz, A-8010 Graz - Austria

• Tipo de documento: Artigo Científico
• Fonte: Synlett; v. 27, n. 1, p. 83-87, JAN 2016.
• Citações Web of Science: 15

Resumo

A continuous Bucherer-Bergs hydantoin synthesis utilizing intensified conditions is reported. The methodology is characterized by a two-feed flow approach to independently feed the organic substrate and the aqueous reagent solution. The increased interfacial area of the biphasic reaction mixture and the lack of headspace enabled almost quantitative conversions within ca. 30 minutes at 120 degrees C and 20 bar even for unpolar starting materials. In addition, a selective N(3)-monoalkylation of the resulting heterocycles under batch microwave conditions is reported yielding potential acetylcholinesterase inhibitors. (AU)

• Processo FAPESP: 14/21319-8 - Avaliação de reatores em fluxo contínuo na síntese de derivados de hidantoínas, imidazolidinonas e oxazolidinonas
• Beneficiário: Júlia Lammoglia Monteiro
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado Direto