59874-94-1Relevant academic research and scientific papers
Microwave-promoted tandem reactions for the synthesis of bicyclic γ-lactams
McGonagle, Fiona I.,Brown, Lindsay,Cooke, Andrew,Sutherland, Andrew
, p. 2330 - 2332 (2011)
A microwave-promoted three-step tandem process for the synthesis of bicyclic γ-lactams is developed. In all cases examined this led to significantly faster tandem processes producing the bicyclic γ-lactams more cleanly and reproducibly compared to standard thermal conditions.
Palladium-Catalyzed [1,3]-O-to-N Rearrangement of Allylic -Imidates
Kuroda, Yusuke
supporting information, p. 98 - 102 (2021/12/02)
The rearrangement of allylic imidates is a powerful transformation for the synthesis of allylic amines. Whereas the [3,3]-rearrangement has long been established as the Overman rearrangement, the corresponding [1,3]-rearrangement is rare. Here, we report
Hypervalent-iodine-mediated ring-contraction monofluorination affording monofluorinated five-membered ring-fused oxazolines
Han, Yong-Chao,Zhang, Yan-Dong,Jia, Qun,Cui, Jian,Zhang, Chi
supporting information, p. 5300 - 5303 (2017/11/06)
The first ring-contraction monofluorination reaction mediated by a hypervalent iodine reagent is reported, and the use of the reaction for the synthesis of monofluorinated five-membered ring-fused oxazolines is described. By means of this reaction, a fluorine atom can be selectively introduced either on the five-membered ring or external to it, depending on whether or not the substrate has C-4 alkyl substituents. The reaction was used for the further conversion of probenecid and isoxepac.
Tandem catalysis of ring-closing metathesis/ atom transfer radical reactions with homobimetallic ruthenium-arene complexes
Borguet, Yannick,Sauvage, Xavier,Zaragoza, Guillermo,Demonceau, Albert,Delaude, Lionel
, p. 1167 - 1173 (2011/04/15)
The tandem catalysis of ring-closing metathesis/atom transfer radical reactions was investigated with the homobimetallic ruthenium-indenylidene complex [(p-cymene)Ru(μ-Cl)3RuCl(3-phenyl-1-indenylidene)(PCy 3)] (1) to generate active species in situ. The two catalytic processes were first carried out independently in a case study before the whole sequence was optimized and applied to the synthesis of several polyhalogenated bicyclic γ-lactams and lactones from αω-diene substrates bearing trihaloacetamide or trichloroacetate functionalities. The individual steps were carefully monitored by 1H and 31P NMR spectroscopies in order to understand the intimate details of the catalytic cycles. Polyhalogenated substrates and the ethylene released upon metathesis induced the clean transformation of catalyst precursor 1 into the Ru(II)-Ru(III) mixed-valence compound [(p- cymene)Ru(μ-Cl)3RuCl 2(PCy3)], which was found to be an efficient promoter for atom transfer radical reactions under the adopted experimental conditions.
A three-step tandem process for the synthesis of bicyclic γ-lactams
McGonagle, Fiona I.,Brown, Lindsay,Cooke, Andrew,Sutherland, Andrew
experimental part, p. 3418 - 3425 (2010/08/21)
A one-pot, three-step tandem process has been developed for the direct synthesis of functionalised bicyclic [3.3.0], [4.3.0] and [5.3.0] γ-lactams from simple allylic trichloroacetimidates. The process involves a palladium(ii) mediated Overman rearrangement followed by the use of Grubbs first generation complex which catalyzes both a ring closing metathesis reaction and a Kharasch cyclization. As well as exploring the scope of this process for the synthesis of a range of functionalised bicyclic γ-lactams, the use of chiral palladium(ii) catalysts during the Overman rearrangement for the enantioselective synthesis of the bicyclic γ-lactams is also demonstrated. The Royal Society of Chemistry 2010.
NOVEL PHENYLAMINO ISONICOTINAMIDE COMPOUNDS
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Page/Page column 28-29, (2010/04/03)
The invention provides novel compounds according to Formula (I), their manufacture and use for the treatment of hyperproliferative diseases, such as cancer, restenosis and inflammation.(Formula I)
Complementary reactions of allylic carbamates using palladium(II): Formation of oxazolidinones or allylic amides from a common precursor
Christie, Steven D. R.,Warrington, Adam D.,Lunniss, Christopher J.
experimental part, p. 148 - 154 (2009/06/18)
The use of palladium to effect two different reactions on a common starting material is presented. With a copper oxidant, an aminohalogenation is achieved to produce oxazolidinones. When the copper is absent, a [3,3]-sigmatropic rearrangement takes place
A tandem aza-claisen rearrangement and ring closing metathesis reaction for the synthesis of cyclic allylic trichloroacetamides
Swift, Michael D.,Sutherland, Andrew
, p. 5239 - 5242 (2008/09/17)
(Chemical Equation Presented) A one-pot tandem palladium(II)-catalyzed aza-Claisen rearrangement and ring closing metathesis process has been developed for the efficient synthesis of cyclic allylic trichloroacetamides. The use of chiral Pd(II) catalysts such as (S)-COP-Cl during the rearrangement stage results in the preparation of these compounds in excellent yields and in high enantiomeric excess.
cis- and trans-Stereoselective Epoxidation of N-Protected 2-Cyclohexen-1-ylamines
O'Brien, Peter,Childs, Amanda C.,Ensor, Gareth J.,Hill, Cheryl L.,Kirby, Jonathan P.,Dearden, Michael J.,Oxenford, Sally J.,Rosser, Clare M.
, p. 4955 - 4957 (2007/10/03)
(Equation Presented) The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better ci
Effect of Temperature on Atom Transfer Cyclization Reactions of Allylic α-Iodo Esters and Amides
Curran, Dennis P.,Tamine, John
, p. 2746 - 2750 (2007/10/02)
Atom-transfer cyclizations of allyl iodoacetates and N-allyl-N-methyliodoacetamides are much more efficient at 80 deg C than at 25 deg C.At 80 deg C, β-(iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10percent hexabutylditin in benzene for 10-60 min).It is proposed that this temperature effect is responsible for some unusual observations by Jolly and Livinghouse in the cyclization of N-cyclohexenyl-N-methyliodoacetamide.The results suggest that the beneficial effect of temperature arises because an increase in the rate of rotation of t he OC-O or OC-N bond in the intermediate radicals begins to convert syn radicals (which cannot cyclize) to anti radicals (which can cyclize).Consistent with this hypothesis, the radical derived from N,N-diallyliodoacetamide (which always has a favorable arrangement for cyclization) closes with excellent efficiency at 25 deg C.
