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Basic Ionic Liquid Promoted Domino Knoevenagel–Thia‐Michael Reaction: An Efficient and Multicomponent Strategy for Synthesis of 1,3‐Thiazines
Author(s) -
Siddiqui I. R.,
Shamim Shayna,
Rai Pragati,
Waseem Malik A.,
Srivastava Arjita,
Srivastava Anjali
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2379
Subject(s) - knoevenagel condensation , chemistry , ionic liquid , aldehyde , ethyl cyanoacetate , yield (engineering) , malononitrile , michael reaction , atom economy , domino , reactivity (psychology) , organic chemistry , combinatorial chemistry , condensation , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy , physics , thermodynamics
An efficient, three‐component strategy for synthesis of 1,3‐thiazines with high atom economy in one‐pot mediated by room temperature basic ionic liquid is described here. The strategy involves basic ionic liquid, [bmim]OH‐catalyzed Knoevenagel condensation between ethyl cyanoacetate and aromatic aldehyde and subsequent thia‐Michael addition with substituted thioureas. The reaction sequence is smooth and quantitative under ambient temperature. [bmim]OH was recovered and reused four times without any appreciable decrease in its reactivity and product yield.