Please use this identifier to cite or link to this item: http://hdl.handle.net/10773/20280
Title: Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
Author: Talhi, Oualid
Pinto, Diana C. G. A.
Almeida Paz, Filipe A.
Hamdi, Maamar
Silva, Artur M. S.
Keywords: spiro bisheterocycles
oxygen and nitrogen heterocycles
bisnucleophiles
NMR
X-ray diffraction
Issue Date: 2015
Publisher: GEORG THIEME VERLAG KG
Abstract: A facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.
Peer review: yes
URI: http://hdl.handle.net/10773/20280
DOI: 10.1055/s-0034-1379613
ISSN: 0936-5214
Publisher Version: 10.1055/s-0034-1379613
Appears in Collections:CICECO - Artigos



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