13196-40-2Relevant academic research and scientific papers
Synthesis of some new 2-substituted-4-sulfamoylphenylazo-thiophene and/or thiazole derivatives as antibacterial agents
Fadda, Ahmed A.,El-Badraw, Afnan M.,Refat, Hala M.,Abdel-Latif, Ehab
, p. 778 - 785 (2016)
Benzoylacetone has been reacted with phenyl isothiocyanate to afford two different thiocarbamoyl derivatives (α-phenylthiocarbamoyl benzoylacetone and benzoyl thioacetanilide) depending upon the base used to perform the reaction. Several new 2-substituted
One-pot three-component heteroannulation of β-oxo dithioesters, amines and hydroxylamine: Regioselective, facile and straightforward entry to 5-substituted 3-aminoisoxazoles
Samai, Subhasis,Chanda, Tanmoy,Ila, Hiriyakkanavar,Singh, Maya Shankar
supporting information, p. 4026 - 4031 (2013/07/19)
An efficient and highly regioselective one-pot three-component synthesis of previously inaccessible and synthetically demanding 3-(cycloalkyl/alkyl/ arylamino)-5-aryl/alkylisoxazoles has been achieved by the cyclocondensation of β-oxo dithioesters, amines and hydroxylamine in ethanol at reflux. This transformation proceeds via an in situ generated β-oxothioamide by the reaction of the β-oxo dithioester and amine, which undergoes nucleophilic attack by hydroxylamine followed by intramolecular cyclization with the oxo functionality and subsequent dehydration to give 5-substituted 3-aminoisoxazoles as a single regioisomer in good yields. Furthermore, the mechanism of the reaction has been established experimentally and shown to be in agreement with the hard and soft (Lewis) acid and base (HSAB) theory. A highly regioselective synthesis of 5-substituted 3-aminoisoxazoles has been achieved by a one-pot three-component coupling of β-oxo dithioesters, amines and hydroxylamine in ethanol at reflux via an in situ generated β-oxo thioamide intermediate. The mechanism of the reaction has been established experimentally and shown to be in agreement with the HSAB theory. Copyright
Sulfur-Containing Heterocycles Derived by Reaction of ω-Keto Amides with Lawesson's Reagent
Nishio, Takehiko
, p. 1207 - 1214 (2007/10/03)
The reaction of ω-keto amides with Lawesson's reagent (LR: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) is described. Treatment of 3-keto amides (2-acylacetamides) 1 with LR gave the corresponding 3-keto thioamides 2, along with 1,2-dithiole-3-thiones 3. Treatment of 4-keto amides, 3-acyl propionamides 5, with LR yielded five-membered heterocycles, pyrroles 6 and/or 2-aminothiophenes 7. 5-Keto amides, 3-benzoyl butyramides 8, reacted with LR to give dihydrothiopyran-2-thione 9 as the sole product, but in low yield. 2-Acylbenzamides 10 also reacted with LR to afford 3-mercaptoisoindolin-2-ones 11 or dihydroisobenzothiophene-1-thiones 12.
POLYCARBONYL HETEROCYCLES. PART VIII. A NEW METHOD FOR THE PREPARATION OF 4-TRIFLUOROMETHYLTHIO-3-PYRAZOLINE-5-THIONE DERIVATIVES FROM 1H-PYRROLE-2,3-DIONE DERIVATIVES VIA NICKEL COMPLEXES.
Zaleska, Barbara,Kurdziel, Magdalena
, p. 1863 - 1874 (2007/10/02)
For the first time, 4-trifluoromethylthio-3-pyrazoline-5-thione derivatives 4 were synthesized by the reaction of trifluoromethylsulfenyl chloride with nickel complexes of β-aminothiocinnamic anilide 3.Complexes 2 and 3 were obtained from 5-aryl-4-thiocarbamoyl-1H-pyrrole-2,3-dione 1.The structure of products 4 has been elucidated on the basis of the elemental analysis and IR, MS, 1H, 19F, 13C NMR spectra.
