Synthesis of 4-Amino-8-cyanoquinazolines from Enones and Enals

Green Method for the Synthesis of Highly Substituted Cyclohexa-1,3-diene, Polyhydroindene, Polyhydronaphthalene, Isochromene, Isothiochromene, and Isoquinoline Derivatives in Ionic Liquids

“…2,6-Dicyanoanilines are typical A−D−A systems, which have been reported to be prepared from arylidenemalonodinitriles and 1-arylethylidenemalonodinitriles in the presence of piperidine or under microwave irradiation . The reactions between propanedinitrile and α, β-unsaturated ketones can also give 2,6-dicyanoanilines, but the yields are very poor . In addition, all above-mentioned reactions need to be performed in organic solvents.…”

Parallel Synthesis of Strongly Fluorescent Polysubstituted 2,6-Dicyanoanilines via Microwave-Promoted Multicomponent Reaction

“…Using this three-component one-pot procedure, we synthesized a parallel library containing 21 polysubstituted 2,6-dicyanoanilines (Table ). The yields (50−63%) are extensively increased as compared with the published methods (5−20%) . The crystallographic structure of compound 4c was determined by X-ray diffraction (see the Supporting Information), which is in accordance with the 1 H NMR, 13 C NMR, and HRMS spectra.…”

“…2,6-Dicyanoanilines were reported to be prepared from arylidenemalonodinitriles and 1-arylethylidenemalonodinitriles in the presence of piperidine 8a. The reaction between propanedinitrile and α,β-unsaturated ketones could also give 2,6-dicyanoanilines, but the yields were very poor (5∼20%) …”

Regioselective Synthesis of Functionally Crowded Benzenes at Room Temperature through Ring Transformation of 2H-Pyran-2-ones

“…18 Although these benzannulation approaches afford a wide variety of aromatic compounds, the utilization of these protocols for the preparation of functionally congested benzenes such as substituted isophthalonitriles places constraints on the choice of reagents or conditions. Aromatic compounds with nitrile and amine functionalities not only possess interesting biological activities 19 but are also useful synthons for their transformation to quinazolines 20 and fluorenones. 21 Although numerous regio-and stereoselective Diels-Alder reactions 22 of 2H-pyran-2-ones with electron-deficient and electron-rich dienophiles do provide benzene derivatives, they require forcing thermal reaction conditions to eliminate the carbon dioxide from the adduct and/or are associated with a mixture of positional isomers.…”