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An Unexpected Synthesis of 2,3,4‐Trisubstituted Quinolines from Imino‐Isatin and Acetylenic Esters Catalyzed by Pyridine as an Organocatalyst
Author(s) -
Afkham Amir Arian,
Mokhtari Javad,
Haghighi Ali Javaheri,
Yavari Issa
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801785
Subject(s) - isatin , chemistry , quinoline , pyridine , catalysis , organic chemistry , proton nmr , combinatorial chemistry , medicinal chemistry
In this paper we report an unexpected synthesis of the 2,3,4‐trisubstituted quinoline systems. The reaction between imino‐isatin (synthesized from the reaction of isatin and ammonia (2 M in MeOH)) and dialkylacetylenedicarboxylates proceeds in MeOH at room temperature in the presence of pyridine as an organocatalyst. The structures of all new compounds were corroborated spectroscopically ( 1 H‐ and 13 C‐NMR, and elemental analysis). A plausible mechanism for this type of reaction is proposed.