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1,8‐Dihydrodithieno[3,4‐ b :3′,4′‐ i ]‐1,4,8,11‐tetraaza[14]annulene 4 H ,12 H ‐[1,4,8,11]Tetraazacyclotetradecino[2,3‐ c :9,10‐ c ]‐dithiophene)
Author(s) -
Bastian Heinz,
Breitmaier Eberhard
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851180634
Subject(s) - annulene , chemistry , nickel , alkyl , stereochemistry , medicinal chemistry , alkoxy group , chelation , metal , organic chemistry
1,8‐Dihydrodithieno[3,4‐ b :3′,4′‐ i ]‐1,4,8,11‐tetraaza[14]annulenes (4 H ,12 H ‐[1,4,8,11]Tetraazacyclotetradecino[2,3‐ c :9,10‐ c′ ]dithiophenes) The title compounds 3a–h , disubstituted in 6,13 positions by alkyl‐, 3‐hydroxypropyl‐, and ethoxycarbonyl groups, are prepared by cyclocondensation of 3,4‐diaminothiophene ( 1 ) with 2‐alkyl‐3‐ethoxyacroleins ( 2a–f ), 3, 4‐dihydro‐2 H ‐pyran‐5‐carbaldehyde ( 2g ), and 2‐(ethoxy‐carbonyl)‐3‐hydroxyacrolein ( 2h ), respectively. Metal template cyclocondensations of the starting materials 1 and 2a–h in the presence of nickel(II) acetate affords the nickel(II) chelates ( 4a–h ) of the macrocyclic N 4 ligands 3 .