A practical synthesis of meso-monosubstituted, β-unsubstituted porphyrins

被引:47
作者
Wiehe, A
Ryppa, C
Senge, MO
机构
[1] Free Univ Berlin, Inst Chem, D-14195 Berlin, Germany
[2] Biolitec AG, D-07745 Jena, Germany
基金
中国国家自然科学基金;
关键词
D O I
10.1021/ol0265867
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic A simple straightforward synthesis for meso-monosubstituted, beta-unsubstituted porphyrins is reported. Porphyrins of this type are easily prepared by condensation of dipyrromethane, pyrrole-2-carbaldehyde, and the desired aromatic or aliphatic aldehyde. The method can be used for a variety of functional groups with yields between 2 and 12%. In most cases, the 5,15-disubstituted porphyrin is obtained as a second product but can be removed easily.
引用
收藏
页码:3807 / 3809
页数:3
相关论文
共 23 条
[1]  
CALLOT HJ, 1978, J CHEM RES-S, P51
[2]  
CAVALEIRO JAS, 1994, HETEROCYCLES, V37, P213
[3]   Electronic factor for photoinduced electron transfer in porphyrin-bridge-quinone systems [J].
do Monte, SA ;
Braga, M .
CHEMICAL PHYSICS LETTERS, 1998, 290 (1-3) :136-142
[4]   ELECTROPHILIC SUBSTITUTION ON PORPHIN .1. NITRATION [J].
DRACH, JE ;
LONGO, FR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3282-3284
[5]   Mechanistic studies on the nucleophilic reaction of porphyrins with organolithium reagents [J].
Feng, XD ;
Bischoff, I ;
Senge, MO .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8693-8700
[6]  
Fischer H, 1936, LIEBIGS ANN CHEM, V521, P157
[7]  
Jaquinod L., 2000, The Porphyrin Handbook-Synthesis and Organic Chemistry, V1, P201
[8]  
KADISH KM, 2000, PROPHYRIN HDB, V1
[9]  
KUZMITSKII VA, 1995, ZH FIZ KHIM+, V69, P276
[10]   ONE-FLASK SYNTHESIS OF MESOSUBSTITUTED DIPYRROMETHANES AND THEIR APPLICATION IN THE SYNTHESIS OF TRANS-SUBSTITUTED PORPHYRIN BUILDING-BLOCKS [J].
LEE, CH ;
LINDSEY, JS .
TETRAHEDRON, 1994, 50 (39) :11427-11440