Biomaterial Database

One-pot synthesis of γ -spiroiminolactones and γ -dispiroiminolactones using N,N'-disubstituted parabanic acid and thioparabanic acid derivatives. 2017

Sakineh Asghari, and Mohammad Qandalee, and Amir Ali Sarmadi

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran. s.asghari@umz.ac.ir.

A direct entry and simple process for the synthesis of [Formula: see text]-spiroiminolactones present in a large number of natural products has been developed. In the first step, the synthesis of parabanic acid derivatives was commenced from the reaction of [Formula: see text]-disubstituted urea and thiourea with oxalyl chloride, then a three-component reaction was carried out with isocyanides, acetylenic esters, and [Formula: see text]-disubstituted parabanic acid derivatives. The method allows the construction of a variety of [Formula: see text]-spiroiminolactone structures in good to high yields starting from readily available precursors. It was found that in the case of [Formula: see text]-diphenyl thioparabanic acid, additional products of [Formula: see text]-dispiroiminolactones have been formed due to the higher electrophilicity of [Formula: see text]-dicarbonyl groups. The structures were fully established using spectroscopic analysis NMR, IR, and Mass spectrometry. The crystal structure of [Formula: see text]-dispiroiminolactone was confirmed from single-crystal X-ray diffraction study.

UI	MeSH Term	Description	Entries
D007783	Lactones	Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES.	Lactone
D008958	Models, Molecular	Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures.	Molecular Models,Model, Molecular,Molecular Model
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D006827	Hydantoins	Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.	Hydantoin,Imidazolidine-2,4-Diones,Imidazolidine 2,4 Diones
D013141	Spiro Compounds	Cyclic compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane, which looks like a bow tie.	Compounds, Spiro
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D060326	Chemistry Techniques, Synthetic	Methods used for the chemical synthesis of compounds. Included under this heading are laboratory methods used to synthesize a variety of chemicals and drugs.	Inorganic Synthesis,Inorganic Synthesis Methods,Inorganic Synthesis Techniques,Methods of Inorganic Synthesis,Methods of Organic Synthesis,Methods of Peptide Synthesis,Organic Synthesis,Organic Synthesis Methods,Organic Synthesis Techniques,Peptide Synthesis Methods,Peptide Synthesis Techniques,Peptide Synthesis, Synthetic,Synthetic Chemistry Techniques,Synthetic Peptide Synthesis,Chemistry Technique, Synthetic,Inorganic Syntheses,Inorganic Synthesis Method,Inorganic Synthesis Technique,Method, Inorganic Synthesis,Method, Organic Synthesis,Method, Peptide Synthesis,Methods, Inorganic Synthesis,Methods, Organic Synthesis,Methods, Peptide Synthesis,Organic Syntheses,Organic Synthesis Technique,Peptide Syntheses, Synthetic,Peptide Synthesis Method,Peptide Synthesis Technique,Syntheses, Inorganic,Syntheses, Organic,Syntheses, Synthetic Peptide,Synthesis Method, Inorganic,Synthesis Method, Peptide,Synthesis Methods, Inorganic,Synthesis Methods, Peptide,Synthesis Technique, Inorganic,Synthesis Technique, Organic,Synthesis Technique, Peptide,Synthesis Techniques, Inorganic,Synthesis Techniques, Organic,Synthesis Techniques, Peptide,Synthesis, Inorganic,Synthesis, Organic,Synthesis, Synthetic Peptide,Synthetic Chemistry Technique,Synthetic Peptide Syntheses,Technique, Inorganic Synthesis,Technique, Organic Synthesis,Technique, Peptide Synthesis,Technique, Synthetic Chemistry,Techniques, Inorganic Synthesis,Techniques, Organic Synthesis,Techniques, Peptide Synthesis,Techniques, Synthetic Chemistry