Study on Acid-Catalyzed Photochemical Reactions of Benzylideneaniline and Azobenzene Derivatives
Date Issued
2005
Date
2005
Author(s)
Li, Tai-Chen
DOI
zh-TW
Abstract
This work mainly studies on the photochemical reaction of benzylideneaniline and azobenzene derivatives, we also studies on the pharmaceutical chemistry of the product from our new reaction.
In benzylideneaniline part, when anhydrous DMF (or DMAC) with saturated hydrogen chloride as a solvent, benzylideneaniline derivatives and analogues can undergo a novel photoalkylation, there have a new carbon-carbon bond formation between benzylideneaniline and N-methyl from DMF (or DMAC). The mechanism of photoalkylation in Schiff’s base has been considered about radical intermedium or single electron transfer in the pass, and therefore we proposed the mechanism of our reaction, involved DMF (or DMAC) transfer an electron to the protonated and excited benzylideneaniline derivatives by irradiation, and finally the combination of radical intermediums to obtain a new series of products.
In azobenzene part, when ethanol as a solvent, azobenzene derivative can undergo a new photocycloaddition to obtain 10,11-dihydro-5H- dibenzo[b,e][1,4]diazepine derivatives by 1.2 M hydrochloric acid catalyzed. The mechanism of this reaction may be proposed for the azobenzene derivatives become trans structure after getting proton, and then may become the four member ring transition state, including two nitrogen atoms. The nitrogen atom attract to ethanol in the transition state, the four member ring was open, then cyclized to obtain 10,11-dihydro- 5H-dibenzo[b,e][1,4]diazepine derivatives.
The synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine deriva- tives and their activity as acetylcholinesterase and pseudocholinesterase inhibitors are described. The drug with that ability is usually in treatment of Alzheimer, myasthenis gravis and some diseases about the neuromuscular transmission.
Subjects
光化學
偶氮苯
苯亞甲基苯胺
Photochemical Reactions
Benzylideneaniline
Azobenzene
Type
thesis
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