Salgado, Arturo R. M. published the artcileSynthesis of endo-fused 5-unsubstituted Hexahydro-2H-pyrano[3,2-c]quinolines via Sequential Sc(OTf)3-catalyzed Cationic Imino-Diels-Alder Reaction/N-debenzylation using N-benzylanilines, 3,4-dihydro-2H-pyran and Paraformaldehyde under MW Irradiation, HPLC of Formula: 1885-29-6, the main research area is hexahydropyranoquinoline preparation diastereoselective microwave irradiation; benzylaniline dihydropyran paraformaldehyde Diels Alder debenzylation scandium triflate catalyst; 2- c]quinolones.; Cationic imine Diels-Alder; Lewis acid catalysis; N-debenzylation; microwave irradiation; pyrano[3; scandium triflate.
Hexahydro-2H-pyrano[3,2-c]quinolines I (R = H; R1 = H, Cl, OMe, OH, etc.; RR1 = -(OCH2O)-; R2 = H; R1R2 = -(OCH2O)-; R3 = H, CN, OMe) are known to have antibacterial, antifungal, and antitumor properties. Great efforts have been made to develop new synthetic methods that lead to the synthesis of valuable libraries. Extensive methodologies, low yields, excessive amounts of catalyst and expensive reactants are some of the limitations of current methodologies. A useful and efficient method to construct diversely substituted hexahydro-2Hpyrano[3,2-c]quinolines I into good to excellent yields through a cationic imino-Diels-Alder/N-debenzylation methodol. is developed. The cationic imino-Diels-Alder/N-debenzylation methodol. was used for the preparation of substituted hexahydro-2H-pyrano[3,2-c]quinolines I. It involves the use of Sc(OTf)3 for activation of cationic imino- Diels-Alder cycloaddition reaction of N-benzylanilines R4NHBn (R4 = Ph, 2H-1,3-benzodioxol-5-yl, 2,4-dimethoxyphenyl, etc.), 3,4-dihydro-2H-pyran and paraformaldehyde in MeCN; and microwave irradiation to shorten reaction time to afford new 6-benzyl-hexahydro-2H-pyrano[3,2- c]quinolines I whose catalytic transfer debenzylation reactions with HCO2NH4 in the presence of Pd/C (10%) and methanol give the new 5-unsubstituted pyrano[3,2-c]quinolines I in excellent yields. An efficient method to synthesize hexahydro-2H-pyrano[3,2-c]quinolines I via the cationic imino-Diels-Alder/N-debenzylation methodol. using Sc(OTf)3 0.5% as Lewis Acid catalyst was described. Excellent yields of the products, use of MW irradiation, short times of reactions, and an efficient and highly diversified method are some of the main advantages of this new protocol.
Current Organic Synthesis published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent) (benzyl). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, HPLC of Formula: 1885-29-6.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts