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以红紫素-18甲酯及其N-甲氧基二酰亚胺甲酯为起始原料,以氧化苯甲腈或者甲亚胺作为1,3-偶极体,与红紫素-18的3-位乙烯基进行偶极环加成反应,在周环上建立了不同的五元杂环结构;选择芳胺和芳醛缩合而成的含氮二烯与红紫素-18二酰亚胺C(3)-双键实施杂Diels-Alder反应(Povarov反应),得到了3-位芳酰基或者芳烷基取代的开环重排产物;利用20-meso-氢和C(12)-甲基的反应活性,在红紫素-18的二氢卟吩色基上分别完成了亲电取代、空气氧化和类羟醛缩合反应,并在周环的12-和20-位上引进了不同的取代基团,合成了一系列未见报道的叶绿素类二氢卟吩衍生物.其化学结构均经UV,IR,1H NMR,MS及元素分析予以证实.同时,对所涉及的反应机理也进行了相应的讨论.
To purple purpurin-18 methyl ester and its N-methoxy imide methyl ester as the starting material, with oxidized benzonitrile or azomethine as a 1,3-dipole body, and purpurin-18 Of the vinyl ring 3-position dipolar cycloaddition reaction in the ring to establish a different five-membered heterocyclic structure; aromatic amines and aryl aldehydes condensation of nitrogen-containing diene and purpurin-18 diacyl Hetero Diels-Alder reaction (Povarov reaction) of the imine C (3) -double bond gives a 3-position aroyl or aralkyl substituted ring-opening rearrangement product; - methyl reactivity, electrophilic substitution, air oxidation and aldol reactions were completed on the chlorin base of purpurogen-18 and introduced at the 12- and 20-positions of the pericyclic ring A series of unreported chlorophyllin chlorin derivatives were synthesized and their chemical structures were confirmed by UV, IR, 1H NMR, MS and elemental analysis.At the same time, The mechanism has also been discussed accordingly.