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RESEARCH PRODUCT
ChemInform Abstract: Cycloaddition of Benzothiete and Electron-Deficient Nitriles.
Herbert MeierM. SchmidtSadiq A. Salehsubject
chemistry.chemical_classificationchemistry.chemical_compoundDouble bondchemistryNitrileStereochemistryGeneral MedicineElectronCleavage (embryo)Electron systemRing (chemistry)Medicinal chemistryCycloadditiondescription
The o-quinoid 8π electron system 2, generated by thermal ring opening of benzothiete (1), enters regio-specific [8π + 2π] cycloaddition reactions with electron-deficient nitriles 3a-d, yielding the 4H-1,3-benzothiazines 4a-d. A competitive dimerization of 1 leads to 1,5-dibenzo[b,f]dithiocin (5). Depending on the nitrile further competitive or subsequent reactions (2 + 3b 7b, 2 + 3d 4d 8d) can occur. The cycloadducts 10e and 11e gained from 3e anticipate a primary cleavage of 3e to methylisothiocyanate 9e which reacts at the CN double bond as well as at the CS double bond.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-08-22 | ChemInform |