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Conversion of Some 2(3 H )‐Furanones into Pyrrolinotriazine and Oxazolopyrimidine Derivatives
Author(s) -
AbouElmagd Wael S. I.,
Hashem Ahmed I.
Publication year - 2012
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.889
Subject(s) - chemistry , thionyl chloride , hydrazine (antidepressant) , ring (chemistry) , benzaldehyde , glycine , ethanol , organic chemistry , hydrate , pyrimidine , medicinal chemistry , pyrazole , urea , chloride , catalysis , amino acid , stereochemistry , biochemistry , chromatography
2(3 H )‐Furanones 1 were utilized for the construction of pyrrolinotriazine and oxazolopyrimidine derivatives 4 and 9 . Thus, 1 reacted with glycine in ethanol at 70°C to give the acids 2 , which were cyclized into the pyrrolin‐5‐one derivatives 3 by the action of HCl/AcOH. The later compounds 3 were also obtained by refluxing the furanones 1 with glycine in glacial AcOH for 10 h. The carboxy functionality in 3 was used for the construction of a triazinone ring by treatment with thionyl chloride followed by refluxing the acid chloride with hydrazine in ethanol. The conversion of the furanones 1 into the oxazolopyrimidine derivatives 9 involved the following steps: (i) ring opening of the lactone ring with hydrazine hydrate to give the acid hydrazides 5 , (ii) conversion of the hydrazides 5 into the corresponding acyl azides 6 by action of NaNO2/AcOH, (iv) base‐catalyzed decomposition of the azides in the presence of glycine, (v) ring closure of the urea derivatives 7 into the pyrimidine derivatives 8 , and finally (vi) condensing 8 with benzaldehyde in the presence of NaOAc/AcOH mixture.