Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1929-1938.DOI: 10.6023/cjoc201503050 Previous Articles     Next Articles



张珠a, 姜齐永a, 张千b, 武进b, 王进军a,b   

  1. a 烟台大学文经学院食品与生物工程系 烟台 264005;
    b 烟台大学化学化工学院 烟台 264005
  • 收稿日期:2015-03-31 修回日期:2015-05-15 发布日期:2015-05-26
  • 通讯作者: 王进军
  • 基金资助:

    国家自然科学基金(No. 21272048)资助项目.

Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives

Zhang Zhua, Jiang Qiyonga, Zhang Qianb, Wu Jinb, Wang Jinjuna,b   

  1. a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
    b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005
  • Received:2015-03-31 Revised:2015-05-15 Published:2015-05-26
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272048).

Methyl pheophorbide-a ester was used as starting material, and the chemical reactions, including allomerization, aldol condensation with formaldehyde, nucleophilic addition on the cycloketone, Tiffeneau-demjanov rearrangement with diazomethane, were carried out making use of active reaction regions linked with C-pyrrol subring to establish different carbonyl structures on the exocyclic ring and 12-position. From these new-formed active groups, the novel structures such as nitrogenous heterocycle and spirocycle were formed by condensations with o-phenylenediamine or o-aminobenzaldehyde, 1,3-dipolar cycloaddition with formaldehyde and sarcosine, and other structure transformations. A series of unreported chlorins related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: chlorophyll-a, chlorin, C-pyrrol subring, chemical modification, synthesis