O-N Or N-N Type Smiles Rearrangement:Applications In The Synthesis Of Heterocyclic Compounds

Smiles rearrangement falls under a broad category of in tramolecular aromatic nucleophilic substitution of an appropriately placed nucleophile (Z) onto aromatic rings possessing a strong electron withdrawing group and a leaving group (Y) properly positioned as shown.Benzo[1,4]oxazin-3(4H)-one derivatives are one of the important classes of heterocyclic compounds and have shown to exhibit a substantial amount of biological activities such as anti-inflammatory, antiulcer, antipyretic, antihypertensive, antifungal, as receptor antagonists, potassium channel modulators, antirheumatic agents and antihypertensive agents, ranging from herbicides and fungicides to therapeutical usable drugs. A facile and efficient approach to1,4-benzooxazinone or1,4-pyridooxazinone and Benzodiazepines scaffolds are developed via Smiles rearrangement tandem reaction.1,4-Benzooxazinones or1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. A series of Benzodiazepines were synthesized in the presence of cesium carbonate at high temperature in yields.The reaction mechanism is assumed by a tandem coupling/Smiles rearrangement/cyclizati on process.In this thesis, two series of1,4-benzooxazinone or1,4-pyridooxazinone scaffolds and Benzodiazepines derivatives were synthesized. These compounds have great biological activites for use as drugs.