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Synthesis of four series of quinoline‐based heterocycles by reacting 2‐chloroquinoline‐3‐carbonitriles with various types of isocyanides
Author(s) -
Tanbakouchian Zahra,
Zolfigol Mohammad Ali,
Notash Behrouz,
Ranjbar Maryam,
Shiri Morteza
Publication year - 2019
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5024
Subject(s) - chemistry , isocyanide , quinoline , aryl , alkyl , organic chemistry , medicinal chemistry , combinatorial chemistry
Four distinct sets of functionalized quinolines were synthesized by reacting 2‐chloroquinoline‐3‐carbonitriles with various types of isocyanides under appropriate conditions. The palladium‐catalysed reaction of less hindered aliphatic and aromatic isocyanides with 2‐chloroquinoline‐3‐carbonitriles yielded 2‐alkyl(aryl)‐1‐imino‐1 H ‐pyrrolo[3,4‐ b ]quinolin‐3(2 H )‐one derivatives; however, the catalysed reaction of more hindered isocyanides such as tert ‐butyl isocyanide produced the corresponding 3‐cyanoquinoline‐2‐carboxamides. Interestingly, chloroquinoline‐3‐carbonitriles reacted with ethyl isocyanoacetate in the presence of Cs 2 CO 3 to generate imidazo[1,5‐ a ]quinoline derivatives; notably, tosylmethyl isocyanide under the same conditions formed unprecedented 2‐tosyl‐3‐cyanoquinolines.