Study On The Synthesis Of 3-Amino-biphenyls,4H-benzopyrans And Benzoacridines Compounds In PEG-400 Media

Biaryls and heterocyclic compounds, especially 4H-pyrans and polyhydrobenzoacridine-1-one derivatives have a wide range of biological and pharmacological activities. Heterocyclic compounds and their derivatives as intermediates of pesticides, pharmaceuticals, dyes and other fine chemical products have already been widely applied. Scientists around the world very concerned about the synthesis of these compounds.Low-molecular-weight polyethylene glycol PEG-400 is a common liquid oligomer, it is low-toxic, easily degradable, non-volatile, non-combustible and inexpensive. PEG-400 has a good solubility for most organic and metal organic compounds, moreover,which was stable in acid and alkali condition, oxidation system of O₂ and H₂O₂, redox system of NaBH4. PEG-400 as a new reaction medium has begun to attract more attention. The dissertation focuses on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives using PEG-400 as reaction medium. The thesis is mainly divided into four chapters:Chapter one: the progress of studies on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives, the application of PEG-400 as reaction medium in the organic synthesis in recent years are reviewed.Chapter two: a series of 3-Amino-2,4-dicarbonitrile-5-methylbiphenyl were synthesized by four-component condensation of aromatic aldehyde, malononitrile and acetone in PEG-400 at 100℃.Chapter three: A various of 2-Amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran were obtained by the reaction of aryl aldehydes, malononitrile and dimedone using PEG-400 as reaction medium at rt without catalyst; 2-Amino-3-cyano-7-hydroxy-4-aryl-4H-benzo-pyrans were also synthesized via three-component condensation of resorcinol, malononitrile, and various aldehydes in PEG-400 at 80 oC.Chapter four: A series of benzo[c]acridine-1-ones and benzo[a]acridine-1-ones were synthesized by the reaction of an aldehyde,α-naphthylamine orβ-naphthylamine and dimedone in PEG-400 at 100℃.This method has the advantages of easy work-up, less pollution and environmentally friendly procedure. We obtained the optimum reaction conditions by studing the factors respectively which affect the reactions such as the ratio of raw materials, reaction medium, temperature and time. The structures of all compounds were confirmed by IR, ¹H NMR, ¹³C NMR and Elemental analysis.