72263-17-3Relevant articles and documents
Preparation of Cyclohexenones from Acyclic (Pentadienyl)iron(1+) Cations: Synthetic Studies Directed toward the A-Ring of Dihydrotachysterols
Manful, Charles F.,Donaldson, William A.
, p. 6787 - 6795 (2014)
The reaction of tricarbonyl(3-methylpentadienyl)iron(1+) cation (7) with stabilized carbon nucleophiles affords 4-methyl-5-substituted cyclohexenones. Reaction of 7 with sodium bis[(+)-2-phenylcyclohexyl]malonate afforded a mixture of diastereomers (de = 60 %); the diastereomeric allylic alcohols resulting from Luche reduction of this mixture were separable by column chromatography. Issues in diastereoselectivity in approaches to synthons for the A-ring of the tachysterols from these cyclohexenones are reported. The reaction of (3-methylpentadienyl)Fe(CO)3 + cation (7) with stabilized carbon nucleophiles affords cyclohexenones. Reaction of 7 with a non-racemic C2 chiral nucleophile dihydrotachysterol analogs proceeds with good diastereoselectivity. Issues in diastereoselectivity in approaches to synthons for the A-ring of the tachysterols from these cyclohexenones are reported.
Palladium-Catalyzed [3 + 2]-C-C/N-C Bond-Forming Annulation
Liu, Yang,Mao, Zhongyi,Pradal, Alexandre,Huang, Pei-Qiang,Oble, Julie,Poli, Giovanni
, p. 4057 - 4061 (2018/07/15)
The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji-Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. When the newly formed annulation product carries a properly located o-haloaryl moiety at the nitrogen substituent, a further intramolecular keto α-arylation can join the cascade, thereby forming two new cycles and three new bonds in the same synthetic operation.
BROMODOMAIN INHIBITOR
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Paragraph 0416, (2016/10/31)
The present invention relates to substituted heterocyclic derivative compounds, compositions comprising said compounds, and the use of said compounds and compositions for epigenetic regulation by inhibition of bromodomain-mediated recognition of acetyl lysine regions of proteins, such as histones. Said compositions and methods are useful for the treatment of cancer and neoplastic disease.
Pyrrolidinyl pyridone and pyrazinone analogues as potent inhibitors of prolyl oligopeptidase (POP)
Haffner, Curt D.,Diaz, Caroline J.,Miller, Aaron B.,Reid, Robert A.,Madauss, Kevin P.,Hassell, Annie,Hanlon, Mary H.,Porter, David J.T.,Becherer, J. David,Carter, Luke H.
scheme or table, p. 4360 - 4363 (2009/04/06)
We report the synthesis and in vitro activity of a series of novel pyrrolidinyl pyridones and pyrazinones as potent inhibitors of prolyl oligopeptidase (POP). Within this series, compound 39 was co-crystallized within the catalytic site of a human chimeric POP protein which provided a more detailed understanding of how these inhibitors interacted with the key residues within the catalytic pocket.
Stereoselective synthesis of 2,4-disubstituted butanolides
Lozanova,Ugurchieva,Veselovsky
, p. 130 - 136 (2008/02/08)
A series of 2,4-disubstituted butanolides was prepared based on the trans-stereoselective electrophilic cyclization of substituted N-(pent-4-enoyl)pyrrolidines. The butanolides may be considered as synthons for this type of natural products. Springer Scie
An isomunchnone-based method for the synthesis of highly substituted 2(1H)-pyridones
Padwa, Albert,Sheehan, Scott M.,Straub, Christopher S.
, p. 8648 - 8659 (2007/10/03)
1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p- acetamidobenzenesulfonyl azide and triethylamine. Treatment of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (±)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh2(OAc)4 in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.
Ligand effects in the rhodium(II) catalysed reactions of diazoamides and diazoimides
Miah, Soyfur,Slawin, Alexandra M. Z.,Moody, Christopher J.,Sheehan, Scott M.,Marino Jr., Joseph P.,Semones, Mark A.,Padwa, Albert,Richards, Ian C.
, p. 2489 - 2514 (2007/10/03)
A range of substituted α-diazoamides 1-8 and diazoimides 9-12 was prepared from the corresponding amines or amides. Rhodium(II) catalysed decomposition of the diazoamides resulted in attack on the aromatic ring to give oxindoles or attack on the alkyl group to give either β-lactams or cycloheptapyrrolones. The chemoselectivity of the rhodium carbenoid intermediate was dependent on the metal ligands, fluorinated carboxamides strongly promoting attack on aromatic rings in preference to other processes. Decomposition of the diazoimides resulted in intramolecular attack on the carbonyl group to give an ylide which could be trapped inter- or intramolecularly. X-Ray crystal structures are reported for the diazo compounds 2 and 4, the indoles 17 and 25, the β-lactam 20, the cycloheptapyrrolones 24 and 28, the dimer 29 and the Pictet Spengler product 39.
