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Synthesis of Novel Functionalized Bi‐ and Oligopyridines
Author(s) -
Sielemann Dirk,
Keuper Ralf,
Risch Nikolaus
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/(sici)1099-0690(200002)2000:3<543::aid-ejoc543>3.0.co;2-v
Subject(s) - chemistry , annulation , mannich base , ketone , terpyridine , mannich reaction , combinatorial chemistry , stereochemistry , organic chemistry , metal , catalysis
An annelation reaction is presented in which 1,3‐cyclohexanedione ( 1 ) and Mannich bases 6a , b are used for the preparation of functionalized bipyridines 12a , 13a , 14a and dihydropyridine derivatives 10b , 11b . All these products possess a keto group which will allow further transformations. The same concept was applied for the synthesis of the S‐shaped terpyridine 25 . The reaction of the Mannich base 21 with 1,3‐cyclohexanedione yielded the heptacyclic terpyridine 22 , which is a key intermediate for the synthesis of torands and other tridentate clefts. The ketone 12a was used for the synthesis of the quaterpyridine 26 .