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Synthesis of Azapolycyclic Systems Based on the Indolizino[3,4‐ b ]quinoline Skeleton − A Diastereoselective Entry to Potential Oligodentate Artificial Receptors
Author(s) -
Temme Oliver,
Dickner Tim,
Laschat Sabine,
Fröhlich Roland,
Kotila Sirpa,
Bergander Klaus
Publication year - 1998
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/(sici)1099-0690(199804)1998:4<651::aid-ejoc651>3.0.co;2-z
Subject(s) - chemistry , molecular tweezers , quinoline , imine , stereochemistry , molecule , denticity , amine gas treating , crystal structure , catalysis , organic chemistry , supramolecular chemistry
A convenient diastereoselective synthetic route to the molecular tweezer bis(indolizino[3,4‐ b ]quinolyl)methane 9 and the rigid indolizino[7′,8′:2,3]quinolino[8,7‐ h ]indolizino[8,7‐ b ]quinolines 14 , 15 as potential receptor molecules has been developed, involving double imine condensation followed by Lewis acid catalyzed biscyclization of prolinal‐derived bis(imines) 8 and 13 , respectively. Whereas the use of SnCl 4 leads to the formation of the planar polycycle 15 , the corresponding concave product 14 is formed in the presence of EtAlCl 2 . Both compounds 14 , 15 , as well as tweezer 9 have been characterized by X‐ray crystal‐structure analysis. Although tris(imines) 20 , 24 derived from 1,3,5‐triaminobenzene ( 18 ) and tris(4‐aminophenyl)amine ( 23 ) could be obtained similarly by molecular sieve‐catalyzed condensation, the corresponding triscyclization could not be achieved. However, by attaching preformed indolizino[3,4‐ b ]quinoline subunits 25 and 31 to an aromatic core, the bidentate receptors 30 , 33 and the tentacle molecule 28 were accessible.