2673-23-6Relevant articles and documents
Iodine-Promoted One-pot Synthesis of Highly Substituted 4-Aminopyrroles and Bis-4-aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines
Jalani, Hitesh B.,Mali, Jyotirling R.,Park, Hyejun,Lee, Jae Kyun,Lee, Kiho,Lee, Kyeong,Choi, Yongseok
supporting information, p. 4073 - 4079 (2018/09/25)
An iodine-promoted one-pot synthesis of functionally diverse and highly substituted 4-aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in-situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4-aminopyrroles. This reaction involved the formation of two C?N bonds and one C?C bond by a formal [1+1+3] annulation approach. The present method provides an interesting framework of two 4-aminopyrrole units directly attached to a biphenyl core by the reaction of 4,4′-diacyl biphenyl, amine, and enamine groups. This Hantzsch-type one-pot reaction provides diverse 4-aminopyrroles, which could be useful in medicinal/material chemistry. (Figure presented.).
The 'inverse electron-demand' Diels-Alder reaction in polymer synthesis. Part 2. Some bis(1,2,4-triazines) as potential bis-diene monomers
Bruce, Michael J.,McLean, Gillian A.,Royles, Brodyck J. L.,Smith, David M.,Standring, Paul N.
, p. 1789 - 1796 (2007/10/02)
Synthetic approaches to a series of 5,5'-linked bis(1,2,4-triazines) are described: these are potential monomers in Diels-Alder polymerisation processes.Oxidation of bis(α-bromophenylacetyl) substituted aromatic compounds with dimethyl sulfoxide, or (better) oxidation of diacetyl- or bis(phenylacetyl) substituted aromatic compounds with hydrogen bromide in dimethyl sulfoxide, gives the corresponding bis(1,2-diketones) and bis(α-keto aldehydes); these are converted into 3,3'-bis(methylsulfanyl)-5,5'-arylenebis(1,2,4-triazines) by reaction with S-methylthiosemicarbazide.The methylsulfanyl groups may then be oxidised by standard methods to give the corresponding methylsulfinyl or methylsulfonyl compounds, although the oxidised products show a tendency to decompose on storage.