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Synthesis of Spiropyrazolines via a Pseudo‐Six Component Reaction
Author(s) -
Rezvanian Atieh,
Babashah Maedeh
Publication year - 2019
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.3510
Subject(s) - chemistry , ketene , isatin , hydrazine (antidepressant) , methylene , hydrate , atom economy , knoevenagel condensation , adduct , organic chemistry , combinatorial chemistry , catalysis , chromatography
A novel and eco‐friendly route for the synthesis of highly functionalized spiropyrazolines via a pseudo‐six component reaction of hydrazine hydrate, nitro ketene dithioacetal, isatin, and active methylene under mild condition at room temperature in ethanol media has been developed. The key steps in the synthetic strategy involve the formation of 1,1‐dihydrazino‐2‐nitroethylene from hydrazine hydrate with nitro ketene dithioacetal and its reaction with Knoevenagel adduct derived from the corresponding isatin and active methylene. The reaction is particularly attractive due to features such as high bond‐forming efficiency, optimum convergence, mild condition, atom economy, easy work‐up/purification, and reduced waste production without using any additive.