Abstract
This thesis consists of two parts: (1)Microwave and Ultrasound Accelerated Synthesis of 5-Cyanoindole We have developed a practical and efficient synthesis of 5-cyanoindole based on Russell’s process using microwave and ultrasound irradiation. Taguchi method was used to optimize the reaction conditions for achieving the highest yield of 5-bromoindole. The hydrolysis of sodium 1-acetylindoline-5-bromo-2-sulfonate was accomplished in 3 min and 8 min under microwave irradiation and ultrasonic irradiation respectively as compared to the 20 h conventional reflux method. Furthermore, the microwave-assisted cyanation of 5-bromoindole was accomplished in 6 min versus more than 18 h of thermal heating. Our methods can dramatically reduce the reaction time which, in turn, can increase the turn over rate of production equipment and decrease energy consumption and hence have economic value. (2)Synthesis and the Synthetic Applications of a New Chiral Hydrazine Auxiliary A novel synthetic approach for the preparation of the a chiral hydrazine auxiliary, N-amino-10,10-dimethyl-4-azatricyclo-[5,2,1,01,5]decane, from (+)-camphene in four steps (54% overall yield) has been established. The chiral hydrazone templates were obtained via the condensation of aldehydes and the hydrazine at room temperature. Finally, the hydrazones were stereoselectively alkylated with n-butyllithium at –40oC to give optically active hydrazines in up to 94%~98% and 58%~89% de.
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