36684-30-7Relevant academic research and scientific papers
Reactions of Cyclic Oxalyl Compounds, 35. - Mechanistic Investigation Aided by Isotopic Labeling, 11. - On the Reaction of 4-Benzoyl-5-phenylfuran-2,3-dione with S-Heterocumulenes - Preparative and Mechanistic Aspects
Heilmayer, Werner,Kappe, Oliver C.,Sterk, Heinz,Kollenz, Gert,Peters, Karl,et al.
, p. 2061 - 2068 (2007/10/02)
The furan-2,3-dione 1 combines with N-sulfinylamines or sulfur diimides to afford the pyrrole-2,3-diones 2, while with N-tosylsulfinylamine the (α-iminobenzyl)furandione 3 is obtained. (α-Iminobenzyl)pyrrolediones 4 are formed in the reaction of 2c with N-tosylsulfinylamine or from 3 with N-tosylsulfur diimides.Diisopropylcarbodiimide and the pyrroledione 2c or the (iminobenzyl)furandione 3a undergo cycloaddition reactions accompanied by novel and surprising rearrangements to furnish the bicyclic compounds 5 and 6, respectively.The molecular skeleton of 6 was confirmed by an X-ray diffraction analysis.With the aid of 17O-labeling experiments and 17O-NMR spectroscopy mechanistic pathways including novel rearrangements were made evident. - Key Words: Furan-2,3-diones/ Pyrrol-2,3-diones/ Cumulenes, S-hetero/ Cycloaddition reactions/ 17O Labeling
Reactions of Cyclic Oxalyl Compounds, XXIII. Reactions of Five-membered 2,3-Dioxo Heterocycles with Carbodiimides - a Synthetic Pathway to Hetero Analogues of Deazapurine Systems
Kollenz, Gert,Penn, Gerhard,Ott, Walter,Peters, Karl,Peters, Eva-Maria,et al.
, p. 1310 - 1329 (2007/10/02)
The furandione 1 reacts with diaryl- or arylalkylcarbodiimides to yield 4--2,3-furandiones 5, which isomerize to 2,3-pyrrolediones 2 above 60 deg C. 1, 2, and 5 react with dimethylcarbodiimide under mild conditions (20 deg C, a few minutes) to give the so far unknown pyrrolooxazinediones 7 which reversibly can lose dimethylcarbodiimide to form again 2.Analogously 2,3-thiophenedione 3 and dimethyl- or diisopropylcarbodiimide yield the pyrrolothiazines 8.The basic skeletons of 7 and 8 were determined by X-ray structure analys is of 7a and 8b.On the other hand, the reaction of 1 with diethyl- or diisopropylcarbodiimide leads to furopyrimidines 10.The bicyclic compounds 7, 8, and 10 can be regarded as heteroanalogues of the 7-deazapurine system.The reaction pathways leading to 5, 7, 8, and 10 involve cycloadditions, cycloreversions or fragmentation reactions as well as some surprising new furandione-furandione rearrangements.
Mechanistic Investigations with the Aid of Isotopic Labeling, VIII. Investigations of the Reaction Pathway to Pyrrolopyrimidines from 4-Benzoyl-5-phenyl-2,3-furandione and Aryl Isocyanates
Kollenz, Gert,Penn, Gerhard,Dolenz, Gerhard,Akcamur,Yunus,Peters, Karl,et al.
, p. 1299 - 1309 (2007/10/02)
4-Benzoyl-5-phenyl-2,3-furandione (1) reacts with aryl isocyanates to yield the pyrrolopyrimidines 4 and the 2,3-pyrrolediones 2; using alkyl isocyanates the corresponding 2,3-pyrrolediones 2e - g are formed exclusively.The formation of 4 and 2 inc
