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Studies on heterocyclization of acetoacetanilide
Faculty
Science
Year:
2013
Type of Publication:
Article
Pages:
85-91
Authors:
Sherif, Mohamed, Assy, Mohamed, Yousif, Nabil, Galahom, Mohamed
DOI:
10.1007/s13738-012-0128-x
Journal:
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY SPRINGER
Volume:
10
Research Area:
Chemistry
ISSN
ISI:000313047900010
Keywords :
Heterocyclization, Acetoacetanilide, Pyridine, Pyridazine
Abstract:
Base-induced cyclocondensation of acetoacetanilide (1) and benzoyl isothiocyanate (2) afforded mercaptopyridine (4). Compound 4 reacted with NaOCl in presence of NH4OH/NaOH to produce isothiazolopyridine (6). Heterocyclization of 4 by ethyl bromoacetate and/or phenacyl bromide afforded pyridothiazapene and pyridine derivatives 7, 8, respectively. The synthesis of pyrazolopyridine (9) was achieved by reaction of 4 with hydrazine hydrate. Oxidative cyclization of 4 by Br-2 produced isothiazolopyridine (10). Chlorination of compound 4 yielded isothiazolopyridine dioxide (11). Compound 1 transformed into pyrane derivatives 12 and 13 by reaction with benzylidenemalononitrile and benzylideneacetophenone, respectively. Heterocyclization of compound 1 by ethylcyanoacetate and diethyloxalate afforded pyridine and cyclopentane derivatives 14 and 15, respectively. Compound 1 heterocyclized to indenopyrane (16) or indeno-pyrrole (17) upon reacted with ninhydrin on cold and hot condition, respectively. Heterocyclization of compound 1 and benzilmonohydrazone afforded pyridazine derivative 18. Coupling of 1 with diazonium salt afforded hydrazone 19 which cyclized using CS2/KOH gave pyridazine derivative 20.
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