- Synthesis of dibenzo[e,g]isoindol-1-ones via photoinduced intramolecular annulation of 3,4-diphenyl-1H-pyrrol-2(5H)-ones
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An efficient, oxidant and photocatalyst-free approach for the synthesis of polycyclic-fused isoindolinone derivatives is reported via annulation of 3,4-diphenyl-3-pyrrolin-2-ones along with release of the hydrogen gas under an argon atmosphere in EtOH by
- Kang, Yang,He, Yun,Sui, Jingzhi,Wang, Tao,Liang, Yong,Zhang, Zunting
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- Synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones utilizing pyrrole weinreb amides
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A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki-Miyaura cross-coupling reaction of 2-aryl-1-bromo-1-nitroethenes with arylboronic acids. Some difficulty was encountered in the preparation of arylnitromethanes, thus leading to the exploration of a cross-coupling strategy that proved more useful. A Barton-Zard pyrrole cyclocondensation reaction between 1,2-diaryl-1-nitroethenes and N-methoxy-N-methyl-2-isocyanoacetamide gave the corresponding pyrrole Weinreb amides, which were then converted into the desired 3-pyrrolin-2-ones in two steps. Overall, this method allowed for the construction of 3,4-diaryl-3- pyrrolin-2-ones with complete regiocontrol of the substituents with respect to the lactam carbonyl. The utility of this synthetic methodology was demonstrated by the preparation of eight unsymmetrical and symmetrical 3,4-diaryl-3-pyrrolin- 2-ones including the N-H lactam analogue of the selective COX-II inhibitor, rofecoxib.
- Greger, Jessica G.,Yoon-Miller, Sarah J. P.,Bechtold, Nathan R.,Flewelling, Scott A.,MacDonald, Jacob P.,Downey, Catherine R.,Cohen, Eric A.,Pelkey, Erin T.
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p. 8203 - 8214
(2011/12/04)
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- Synthesis and evaluation of pyrrolin-2-one compounds, a series of plasminogen activator inhibitor-1 inhibitors
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A novel series of furan-2-one and pyrrolin-2-one derivatives having PAI-1 (plasminogen activator inhibitor-1) inhibitory activity were synthesized and evaluated for their antithrombotic activity in a rat arterial thrombosis model. Among the synthesized co
- Miyazaki, Hiroshi,Ogiku, Tsuyoshi,Sai, Hiroshi,Moritani, Yasunori,Ohtani, Akio,Ohmizu, Hiroshi
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experimental part
p. 979 - 985
(2010/03/23)
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- Suzuki-Miyaura cross-coupling approach to 3,4-diaryl-3-pyrrolin-2-ones from tetramic acid triflates
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A three-step approach to 4-aryl-3-phenyl-3-pyrrolin-2-ones from a readily available tetramic acid is described. The introduction of different aryl groups to the 4-position of the ring system was accomplished utilizing Suzuki-Miyaura cross-coupling reactio
- Dorward, Kathryn M.,Guthrie, Nicolette J.,Pelkey, Erin T.
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p. 2317 - 2322
(2008/02/13)
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- Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides
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A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.
- Coffin, Aaron R.,Roussell, Michael A.,Tserlin, Elina,Pelkey, Erin T.
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p. 6678 - 6681
(2007/10/03)
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- A Simple and Convenient Synthesis of 3,4-Diaryl-1,5-dihydro-2H-pyrrol-2-ones
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A simple and convenient synthesis of pharmacologically active five-membered unsaturated γ -lactams from readily available starting materials has been achieved.
- Babu, P. Ramesh,Balasubramanian, T. R.
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- Production of 3-pyrrolin-2-ones
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Pyrrolidin-2-ones are produced by hydrogenation of 3-pyrrolin-2-ones, which latter compounds could not prior to this invention be easily obtained. These 3-pyrrolin-2-ones with various substituents are produced by ring closure of N-aroylmethyl-acetamides.
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- Ring Transformation of 3,4-Diphenyl-2-furylcarbamoyl Compounds to N-Substituted 3,4-Diphenyl-5-hydroxy-3-pyrrolin-2-ones
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3,4-Diphenyl-2-furylcarbamoyls (IIIa - e) react with oxygen in benzene at room temperature and in the abscence of catalysts or bases to give 3,4-diphenyl-5-hydroxy-3-pyrrolin-2-ones (Va - e) as main products.Under the same conditions, treatment of 3,4-diphenyl-2-furyl isocyanate (II) with an excess of various amines resulted in a clean autoxidation reaction to give Ve - h and diphenylmaleimides (XIIa - d) in a ratio of about 1:1. 3-Hydroxyphenantropyrrolin-1-ones (XIIIa - e) were prepared by the photocyclization of Va - e.
- Yakushijin, Kenichi,Kozuka, Masamichi,Furukawa, Hiroshi
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p. 2178 - 2184
(2007/10/02)
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