Premium
21,23‐Dithia‐3,13‐diazaporphycenes − Novel Aromatic Porphycene Analogues Incorporating Thiazole
Author(s) -
Nußbaumer Thomas,
Krieger Claus,
Neidlein Richard
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2449::aid-ejoc2449>3.0.co;2-f
Subject(s) - annulene , chemistry , thiazole , aromaticity , crystal structure , coupling reaction , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , molecule , catalysis
The syntheses of the first examples of aromatic thiazole‐containing porphycene analogues 3 have been accomplished by oxidation of the corresponding 3,20:10,13‐diepithio‐6,9:16,19‐diimino‐1,11‐diaza[20]annulenes 9 with DDQ. Compounds 9a − c have been synthesized by McMurry coupling reaction of the diformylated 2‐(1 H ‐pyrrol‐2‐yl)thiazoles 8a − c , readily available by a three‐step reaction sequence using 2‐pyrrolethiocarboxamide ( 4 ) as starting material. The aromaticity of the 21,23‐dithia‐3,13‐diazaporphycenes 3 is clearly established by NMR and UV/Vis spectroscopy and verified by X‐ray crystal structure analysis of 3b .