93394-39-9Relevant academic research and scientific papers
Synthesis and Photochemistry of 2,2-Dimethyl-3(H)-thiophenone, a Ketonic Tautomer of 3-Hydroxythiophene
Anklam, Elke,Ghaffari-Tabrizi, Ramin,Hombrecher, Hermann,Lau, Sabine,Margaretha, Paul
, p. 1402 - 1405 (1984)
On irradiation (λ = 366 nm), the 4-thia-2-cyclopentenone 3a behaves in complete analogy to the oxa-enone 3c undergoing regio- and stereospecific cyclodimerization, regiospecific cycloaddition with 2-methylpropene and cycloaddition with 2,3-dimethyl-2-butene to afford cyclobutane derivatives.In contrast, the 4-aza-2-cyclopentenone 3b does not undergo the above-mentioned reactions but only slow photocomposition.
3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 8. Reactions of 1-Isopropyl-2,2-dimethyl-1H-pyrrol-3(2H)-one with Electrophiles
McNab, Hamish,Monahan, Lilian C.
, p. 419 - 424 (2007/10/02)
Reaction of the pyrrolone (2) with N-, C-, and halogen-electrophiles takes place at the 4-position to give the azo compounds (3)-(5), the 'methylene Meldrum's' derivative (12) and the halogeno derivatives (16)-(18).Reductive cleavage of the azo compound (5) gives a convenient route to the 4-aminopyrrolone (7), which may be diazotized and coupled with 2-naphthol.Decomposition of the Meldrum's derivative (12) with base leads to the malonates (13) and (14) and acrylate (15).Deuterium exchange at the 5-position takes place when the halogeno compounds (16)-(18) are treated with methoxide in methanol: the 5-anion is thought to be an intermediate.Protodehalogenation of the 4-bromo- and 4-iodo-derivatives (17) and (18) occurs on treatment with triphenylphosphine.
3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 2. Scope and Limitations of the Synthesis of Pyrrol-3-ones by Pyrolysis of Aminomethylene Meldrum's Acid Derivatives.
McNab, Hamish,Monahan, Lilian C.
, p. 863 - 868 (2007/10/02)
Flash vacuum pyrolysis of N,N-disubstituted aminomethylene Meldrum's acid derivatives provides a route to 4,5-unsubstituted 1H-pyrrol-3(2H)-ones by a hydrogen-transfer-cyclisation sequence.Alkyl and aryl 1-substituted, 1,2-disubstituted, and 1,2,2-trisubstituted pyrrolones can be obtained.In competitive cases, there is little selectivity between hydrogen transfer from primary, secondary, or tertiary sites, although benzyl hydrogen atoms proved particularly reactive, giving a general synthesis of 2-phenyl-1H-pyrrol-3(2H)-ones.
