An Unexpected Synthesis of 2,3,4‐Trisubstituted Quinolines from Imino‐Isatin and Acetylenic Esters Catalyzed by Pyridine as an Organocatalyst | Zendy

Afkham Amir Arian | Zendy; Mokhtari Javad | Zendy; Haghighi Ali Javaheri | Zendy; Yavari Issa | Zendy

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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.

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