Studies of the Behavior of 2(3h)-Furanthione and Thionopyrroline Derivatives Toward Some Nitrogen Nucleophiles

Conversion of 2(3H)‐furanones bearing indole nuclei into novel amide, pyrrolone, and imidazole derivatives

“…The preparation of (3E)-1-acetyl-3(5-aryl-2-oxofuran-3(2H)-ylidene)-1,3-dihydro-2H-indol-2-ones 1ad has already been described [19] as part of our previous investigation on 2-(3H)-furanones [20][21][22][23][24]. These form only as E-isomers.…”

Ring Transformation of a 2(3H)‐furanone Derivative into Oxazinone and Pyrimidinone Heterocycles

“…In the last decades, our research group was interested in the conversion of 2(3 H )‐furanones into a variety of heterocyclic systems of synthetic and biological importance. Based on their facile ring opening by nitrogen nucleophiles, these furanones were converted into acyclic products that, via ring closure, afforded many heterocycles, namely, pyrrolones, pyridazinones, triazoles, oxadiazoles, thiazolidinones, and benzoxazinones . To our knowledge, the conversion of 2(3 H )‐furanones into pyrimidine derivatives has not been reported.…”

Arylation of 3-heterylmethylene-5-arylfuran-2(3H)-thiones

“…15 The structure of the latter products was inferred from analytical and spectral data. The IR spectra of 2 (see Experimental) showed the disappearance of the carbonyl stretching frequency and the appearance of a band at 1250-1260 cm -1 attributable to the C=S group.…”

“…For this purpose, the furanones 1 were converted into the thiono derivatives namely 3-heterylmethylene-5-arylfuran-2(3H)-thiones 2 using P 2 S 5 in toluene. 15 The structure of the latter products was inferred from analytical and spectral data. The IR spectra of 2 (see Experimental) showed the disappearance of the carbonyl stretching frequency and the appearance of a band at 1250-1260 cm -1 attributable to the C=S group.…”