烟台大学学报（自然科学与工程版）2012，Vol.25Issue(1)：22-27,6.
具有叶绿素基本碳架的二氢卟吩类衍生物的Gewald反应研究
Gewald Reaction of Chlorine Derivatives with the Basic Skeleton of Chlorophyll
摘要
Abstract
Methyl pyropheophorbide-a 1 is used as starting material and oxidized into chlorine acetal 2 in the yield of 78% by the oxidation for C3-vinyl group with thallium(III) nitrate. The removing for acetal group and carbome-thoxyl group are carried out in one step by refluxing in acetic acid to give 3-formylmethyl-3-devinyl pyropheophorbide-a 3 in 67%. The nitro-group is introduced into 20-meso position by electrophilic substitution to produce nitrified chlorin aldehyde 4. Under alkaline condition the Gewald reaction of 4 with malononitrile and sulfur accomplish the synthesis of chlorine 5 substituted with thiophene ring at 3-position, the same Gewald reaction with carbonyl linked with E-ring just give oxidiazed products. The forming processes of five-membered heterocyclic ring is discussed and the reaction mechanisms are tentatively proposed. The structures of all new compounds are assigned based on the data from IR,1HNMR, MS and elemental analysis.关键词
叶绿素-α/二氢卟吩/脱镁叶绿酸-α甲酯/Gewald反应Key words
chlorophyll-a/chlorin/methyl pheophorbide-a/Gewald reaction分类
化学化工引用本文复制引用
刘冉冉,武进,王振,杨泽,王进军..具有叶绿素基本碳架的二氢卟吩类衍生物的Gewald反应研究[J].烟台大学学报（自然科学与工程版）,2012,25(1):22-27,6.基金项目
山东省自然科学基金资助项目(Y2008B49). （Y2008B49）
