Synthetic applications of 2-allylbenzaldehyde

• Main Authors: Chieh-Kai Chan, 詹傑凱
• Other Authors: Meng-Yang Chang
• Format: Others
• Language: zh-TW
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/81625942672797897599

博士 === 高雄醫學大學 === 醫藥暨應用化學系博士班 === 105 === In this thesis, we have developed a series of synthetic routes toward some bioactive compound derivatives which demonstrate various potential drug activities. These skeletons started from a versatile building block, 2-allylbenzaldehyde, as starting material which was prepared from isovanillin via a three-step protocol with high overall yields. The synthetic applications of 2-allylbenzaldehyde including benzoheterocycles are: (i) Three-step synthesis of substituted isochromenes, (ii) Synthesis of substituted 2,3-benzodiazepines, (iii) Synthesis of polyoxygenated benzo[a,e]cycloheptatrienes, (iv) One-Pot Synthesis of Substituted 1,6-Diarylnaphthalenes via a Tandem Claisen Rear-rangement and Ene Reaction Protocol, (v) CuI-Mediated One-Pot Cycloacetalization/Ketalization Synthesis of Benzobicyclo[3.2.1] acetals and ketals, and (vi) HNO3/H2SO4-mediated One-Pot Construction of Nitrated Benzobicyclo[3.3.1] acetals and ketals via Nitration of o-Carbonyl Allylbenzenes. Some key compounds were characterized and confirmed by X-ray single-crystal diffraction analysis.