128407-54-5Relevant academic research and scientific papers
A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives
Yin, Guodong,Wang, Zihua,Chen, Aihua,Gao, Meng,Wu, Anxin,Pan, Yuanjiang
, p. 3377 - 3383 (2008/09/21)
(Chemical Equation Presented) 2-(Methylthio)-1,4-diaryl-2-butene-1,4-dione (3) are prepared from readily available aryl methyl ketones in the presence of copper(II) oxide, iodine, and dimethyl sulfoxide. The success of the cross-coupling reaction of 4-chloroacetophenone with 2-acetylthiophene confirms a proposed self-sorting tandem reaction mechanism. Both Z- and E-isomers of compound 3 are readily converted into the corresponding 3-methylthio 2,5-diaryl furan 7 in good yield through a domino process involving the reduction of the double bond followed by the Paal-Knorr furan synthesis. Meanwhile, 4-bromo-3-methylthio 2,5-diaryl furan 10 is obtained either by the treatment of furan 7 with molecular bromine or by the treatment of diketone 3 with 30% hydrogen bromide in acetic acid solution in one pot. Removal of the methylthio group is accomplished by the treatment of 7 with Raney Ni in ethanol, which affords the diaryl-substituted furan 11 in excellent isolated yield. Selective reduction of the double bond of compound 3 leads to the formation of the saturated 1,4-diketone 13, which is easily converted to the corresponding 3-methylthio-2,5-diaryl-substituted pyrrole 14 and thiophene 15 via the Paal-Knorr cyclization reaction.
Reactions of 2-(Dialkylamino)arylacetonitriles with Acetylenes Under Basic Conditions. A Simple Synthesis of Substituted Mono and Diketones
Zdrojewski, T.,Jonczyk, A.
, p. 224 - 233 (2007/10/02)
2-(Dialkylamino)arylacetonitriles 1 react with acetylenes 2a,b in dimethyl sulfoxide, powdered sodium hydroxide and triethylbenzylammonium chloride as a catalyst to give 3 and/or 4.The latter are formed via addition of anion 8 to immonium salt 9.The type of product formed depends on the basicity of amino moiety in 3.Furthermore, compound 1 adds to C-1 of acetylene 2c affording the vinyl derivatives 15.The products 3,4,11 and 15 are hydrolyzed to give ketones 5-7,12 and 16, respectively.
