Biomaterial Database

Polymer-supported stereoselective synthesis of tetrahydrobenzopyrazino-thiadiazinone dioxides via N-sulfonyl iminiums. 2014

Naděžda Cankařová, and Agustina La Venia, and Viktor Krchňák

Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17 Listopadu 12, 771 46 Olomouc, Czech Republic.

The stereoselective synthesis of 1,2,11,11a-tetrahydrobenzo[e]pyrazino[1,2-b][1,2,4]thiadiazin-3(4H)-one 6,6-dioxides on a solid support via tandem N-sulfonyl iminium ion cyclization, followed by nucleophilic addition is reported. The synthesis proceeded with full control of stereoselectivity at the newly formed asymmetric carbon, under mild conditions, and using commercially available building blocks. The synthetic route provided high-purity crude products.

UI	MeSH Term	Description	Entries
D007097	Imines	Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group.	Imine
D011108	Polymers	Compounds formed by the joining of smaller, usually repeating, units linked by covalent bonds. These compounds often form large macromolecules (e.g., BIOPOLYMERS; PLASTICS).	Polymer
D011719	Pyrazines	A heterocyclic aromatic organic compound with the chemical formula C4H4N2.	Pyrazine
D003499	Cyclic S-Oxides		Heterocyclic S-Oxides,Cyclic S Oxides,Heterocyclic S Oxides,Oxides, Cyclic S,S Oxides, Cyclic,S-Oxides, Cyclic,S-Oxides, Heterocyclic
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
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
D013450	Sulfones		Sulfone
D013829	Thiadiazines
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular