- Synthesis of Ruscodibenzofuran (8-acetyl-7-hydroxy-1,4-dimethyldibenzofuran)
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A short synthesis of ruscodibenzofuran (1), a dibenzofuran extractive of Ruscus aculeatus, is described, the two significant steps of which exemplify a general route for the conversion of phenols into dibenzofurans.
- Scannell, Ralph T.,Stevenson, Robert
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- Synthetic method of VEGFR inhibitor furoquitinib and benzofuran intermediate thereof
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The invention discloses a synthetic method of a VEGFR inhibitor furoquitinib and a benzofuran intermediate thereof. The synthetic method of the VEGFR inhibitor furoquitinib comprises the following steps of S1, halogenation, S2, acylation, S3, coupling, S4
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Paragraph 0075-0077
(2021/05/01)
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- Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
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The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction.
- Deichert, Julie A.,Mizufune, Hideya,Patel, Jignesh J.,Hurst, Timothy E.,Maheta, Ashish,Kitching, Matthew O.,Ross, Avena C.,Snieckus, Victor
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supporting information
p. 4693 - 4697
(2020/05/08)
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- Synthesis method of 2-bromo-5-methoxyphenol
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The invention discloses a synthesis method of 2-bromo-5-methoxyphenol. According to the synthesis method, 3-methoxyphenol is taken as a raw material, firstly, the 3-methoxyphenol reacts with a protection reagent such as tert-butyldimethylsilyl chloride, a
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- Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
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The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
- Costello, Jeff P.,Ferreira, Eric M.
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supporting information
p. 9934 - 9939
(2019/12/24)
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- Synthesis of 2-arylbenzofuran-3-carbaldehydes: via an organocatalytic [3+2] annulation/oxidative aromatization reaction
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A novel organocatalytic [3+2] annulation/oxidative aromatization reaction of enals with 2-halophenols or β-naphthols is reported. This process enables chemo- and regioselective access to 2-arylbenzofuran-3-carbaldehydes without the use of transition metals or strong oxidants. Preliminary mechanistic studies reveal that an unprecedented, organocatalytic, direct α-arylation pathway is involved.
- Zhang, Huiwen,Ma, Chunmei,Zheng, Ziwei,Sun, Rengwei,Yu, Xinhong,Zhao, Jianhong
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supporting information
p. 4935 - 4938
(2018/05/23)
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- A conceptually novel construction of the 6a-hydroxypterocarpan skeleton – Synthesis of (±)-variabilin
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A new access to the 6a-hydroxypterocarpan variabilin was established. Key step of this concise total synthesis is a challenging cyclization of a haloketone via halogen–metal exchange and subsequent intramolecular addition to the carbonyl function.
- Ciesielski, Philipp,Metz, Peter
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supporting information
p. 6175 - 6177
(2017/09/30)
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- HEMOGLOBIN MODIFIER COMPOUNDS AND USES THEREOF
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Described herein are compounds, including pharmaceutically acceptable salts thereof, methods of making such compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, prevent or diagnose blood-based diseases, disorders or conditions.
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Paragraph 00389
(2018/02/28)
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- Stereoselective Access to 1-[2-Bromo(het)aryloxy]propan-2-amines Using Transaminases and Lipases; Development of a Chemoenzymatic Strategy Toward a Levofloxacin Precursor
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Two independent enzymatic strategies have been developed toward the synthesis of enantioenriched 1-[2-bromo(het)aryloxy]propan-2-amines. With that purpose a series of racemic amines and prochiral ketones have been synthesized from commercially available 2-bromophenols or brominated pyridine derivatives bearing different pattern substitutions in the aromatic ring. Biotransamination experiments have been studied using ketones as starting materials, yielding both the (R)- and (S)-amine enantiomers with high selectivity (91-99% ee) depending on the transaminase source. In a complementary approach, the classical kinetic resolutions of the racemic amines have been investigated using Candida antarctica lipase type B as biocatalyst. Ethyl methoxyacetate was found as a suitable acyl donor leading to the corresponding (S)-amines (90-99% ee) and (R)-amides (88-99% ee) with high selectivity in most of the cases. A preparative biotransamination process has been developed for the synthesis of (2S)-1-(6-bromo-2,3-difluorophenoxy)propan-2-amine in 61% isolated yield after 24 h, a valuable precursor of the antimicrobial agent Levofloxacin.
- Mourelle-Insua, ángela,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente
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p. 9765 - 9774
(2016/10/31)
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- BORONIC ACID DERIVATIVES AND THERAPEUTIC USES THEREOF
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Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents.
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Paragraph 0326
(2016/10/04)
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- Practical regioselective halogenation of vinylogous esters: Synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols
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A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology to access polyhaloresorcinols is also reported. These methods create useful functionalized building blocks for further synthetic applications.
- Chen, Xiaohong,Liu, Xiaoguang,Martinez, Jenny S.,Mohr, Justin T.
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p. 3653 - 3665
(2016/06/06)
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- A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans
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A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.
- Hemelaere, Rémy,Carreaux, Fran?ois,Carboni, Bertrand
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supporting information
p. 2470 - 2481
(2015/04/22)
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- Visible-light photoredox catalysis enabled bromination of phenols and alkenes
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A mild and efficient methodology for the bromination of phenols and alkenes has been developed utilizing visible light-induced photoredox catalysis. The bromine was generated in situ from the oxidation of Br- by Ru(bpy)33+, both of which resulted from the oxidative quenching process.
- Zhao, Yating,Li, Zhe,Yang, Chao,Lin, Run,Xia, Wujiong
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p. 622 - 627
(2014/04/17)
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- Accelerating Ni(ii) precatalyst initiation using reactive ligands and its impact on chain-growth polymerizations
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Nickel(ii) complexes with varying reactive ligands, which were designed to selectively accelerate the initiation rate without influencing the propagation rate in the chain-growth polymerization of π-conjugated monomers, were investigated. Precatalysts with electronically varied reacting groups led to faster initiation rates and narrower molecular weight distributions. Computational studies revealed that the reductive elimination rates are largely modulated by the ability of the two reacting arenes to stabilize the increasing electron density on the catalyst during reductive elimination. Overall, these studies provide insight into a key mechanistic step of cross-coupling reactions (reductive elimination) and highlight the importance of initiation in controlled chain-growth polymerizations.
- Lee, Se Ryeon,Bloom, Jacob W. G.,Wheeler, Steven E.,McNeil, Anne J.
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supporting information
p. 4218 - 4222
(2013/04/10)
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- Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones
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Unexpected Smiles! An unusual and highly regioselective synthesis of dibenzoxazepinones by a domino sequence assisted by an unexpected Smiles rearrangement is reported. The process is effective on electronically differentiated phenols and shows a high tolerance to variation in the benzamide substituents. A plausible path for the reaction, supported by preliminary mechanistic data, is offered. Copyright
- Kitching, Matthew O.,Hurst, Timothy E.,Snieckus, Victor
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supporting information; experimental part
p. 2925 - 2929
(2012/05/04)
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- TETRACYCLIC XANTHENE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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The present invention relates to novel Tetracyclic Xanthene Derivatives of Formula (I) and pharmaceutically acceptable salts thereof, wherein A, Y1, Y2, Z, Ra, Rb, R1a, R1b and R2 are as defined herein. The present invention also relates to compositions comprising at least one Tetracyclic Xanthene Derivative, and methods of using the Tetracyclic Xanthene Derivatives for treating or preventing HCV infection in a patient.
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Page/Page column 80
(2012/10/07)
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- TETRACYCLIC XANTHENE DERIVATIVES AND METHODS OF USE THEREOF FOR TREATMENT OF VIRAL DISEASES
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The present invention discloses tetracyclic xanthene derivatives of Formula (I) and pharmaceutically acceptable salts thereof, wherein A, Y1, Y2, Z, Ra, Rb, R1a, R1b, and R2 are as defined herein. The present invention also discloses compositions comprising at least one tetracyclic xanthene derivative, and methods of using the tetracyclic xanthene derivatives for treating or preventing HCV infection in a patient.
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Page/Page column 99
(2012/10/07)
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- Simple and improved regioselective brominations of aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxodisulfate in the presence of potassium bromide under mild reactions conditions
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A simple, efficient, and mild method for the selective bromination of some activated aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxodisulfate in the presence of potassium bromide in non-aqueous solution is reported. The results obtained revealed good to excellent selectivity between the ortho and para positions of phenols and methoxyarenes.
- Ghasemnejad-Bosra, Hassan,Ramzanian-Lehmali, Farhad,Jafari, Somaye
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experimental part
p. 685 - 692
(2012/01/16)
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- Synthetic access to optically active isoflavans by using allylic substitution
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A general approach to the (S)- and (R)-isoflavans was invented, and efficiency of the method was demonstrated by the synthesis of (S)-equol ((S)-3), (R)-sativan ((R)-4), and (R)-vestitol ((R)-5). The key step is the allylic substitution of (S)-6a (Ar1=2,4-(MeO)2C6H3) and (R)-6b (Ar1=2,4-(BnO)2C6H3) with copper reagents derived from CuBr·Me2S and Ar2-MgBr (7a, Ar2=4-MeOC6H4; 7b, 2,4-(MeO)2C6H3; 7c, 2-MOMO-4-MeOC6H3), furnishing anti SN2′ products (R)-8a and (S)-8b,c with 93-97% chirality transfer in 60-75% yields. The olefinic part of the products was oxidatively cleaved and the Me and Bn groups on the Ar1 moieties was then removed. Finally, phenol bromide 9a and phenol alcohols 9b,c underwent cyclization with K2CO3 and the Mitsunobu reagent to afford (S)-3 and (R)-4 and -5, respectively.
- Takashima, Yuji,Kaneko, Yuki,Kobayashi, Yuichi
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experimental part
p. 197 - 207
(2010/03/03)
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- 1,2,4-OXADIAZOL DERIVATIVES, THEIR PHARMACEUTICAL COMPOSITIONS AND THEIR USE AS SPHINGOSINE 1-PHOSPHATE 1 RECEPTOR AGONISTS
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1,2,4-Oxadiazol derivatives represented by formula (I) useful as sphingosine 1-phosphate 1 (S1P1) receptor agonists, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders mediated via S1P1 receptor are disclosed.
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Page/Page column 43-44
(2010/12/31)
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- Bromination of some aromatic compounds with potassium bromide in the presence of benzyltriphenylphosphonium peroxodisulfate
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A simple, efficient, and mild method for selective bromination of some activated aromatic compounds using potassium bromide in the presence of benzyltriphenylphosphonium peroxodisulfate in nonaqueous solution is reported. The results obtained revealed good to excellent selectivity between ortho and para positions of phenols and methoxyarenes. Copyright Taylor & Francis Group, LLC.
- Tajik, Hassan,Mohammadpoor-Baltork, Iraj,Albadi, Jalal
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p. 323 - 328
(2007/10/03)
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- Total synthesis of phalarine
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(Chemical Equation Presented) End of the expedition ... for now: Completion of the first total synthesis of phalarine from an advanced rearrangement product brought up interesting obstacles to overcome. Use of the Gassman oxindole synthesis and subsequent
- Li, Chaomin,Chan, Collin,Heimann, Annekatrin C.,Danishefsky, Samuel J.
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p. 1448 - 1450
(2008/03/15)
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- Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists
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The present invention provides serotonergic aminoalkylbenzofurans of Formula (I): where R, R1, R2, R3, R4, R4′, R5, R5′, and R12 are as described in the specification.
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Page/Page column 19
(2010/11/08)
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- A New Approach to Rapid Parallel Development of Four Neurokinin Antagonists. Part 4. Synthesis of ZD2249 Methoxy Sulfoxide
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The manufacture of ZD2249 methoxy sulfoxide (1) using a new project approach is described. Research department processes were scaled up to 100 L if process safety and robustness were not compromised; other factors were treated according to the new approach. Using this strategy, we were able to manufacture a key intermediate on sufficient scale to support delivery of 1 kg quantities of bulk drug within 6 months of the start of lab work.
- Bowden, Sharon A.,Nigel Burke,Gray, Fiona,McKown, Steven,Moseley, Jonathan D.,Moss, William O.,Murray, Paul M.,Welham, Matthew J.,Young, Maureen J.
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- SEROTONERGIC BENZOFURANS
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The present invention provides serotonergic benzofurans of Formula (I): where A, R, R, R, R, and R are as described in the specification.
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Page/Page column 14
(2010/02/04)
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- Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination
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(Matrix presented) The catalytic combination of Pd2(dba) 3/HP(t-Bu)3·BF4 and DABCO gives an unusual intramolecular Heck reaction with dihydronaphthalene substrates, yielding formal anti-hydride elimination produ
- Lautens, Mark,Fang, Yuan-Qing
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p. 3679 - 3682
(2007/10/03)
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- Design, synthesis, and SAR of tachykinin antagonists: Modulation of balance in NK1/NK2 receptor antagonist activity
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Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.
- Albert, Jeffrey S.,Andisik, Donald,Barthlow, Herbert,Bernstein, Peter R.,Bialecki, Russell A.,Dedinas, Robert,Dembofsky, Bruce T.,Hill, Daniel,Kirkland, Karin,Koether, Gerard M.,Kosmider, Benedict J.,Ohnmacht, Cyrus,Palmer, William,Potts, William,Rumsey, William,Shen, Lihong,Shenvi, Ashok,Sherwood, Scott,Aharony, David,Warwick, Paul J.,Russell, Keith
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p. 3972 - 3983
(2007/10/03)
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- N-SUBSTITUTED NAPHTHALENE CARBOXAMIDES AS NEUROKININ-RECEPTOR ANTAGONISTS
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A compound of formula I wherein: R is alkyl; R1 is optionally substituted phenyl 2-oxo-tetrahydro-1(2H)-pyrimidinyl, or 2-oxo-1-piperidinyl; R2 is hydrogen, alkoxy, alkanoyloxy, alkoxycarbonyl, alkanoylamino, acyl, alkyl, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl where the alkyl groups are the same or different, hydroxy, thioacyl, thiocarbamoyl, N-alkylthiocarbamoyl, or N,N-dialkylthiocarbamoyl where the alkyl groups are the same or different. X1 and X2 are independently hydrogen or halo, provided that at least one of X1 or X2 is halo; and R3, R4, R5 and R6 are independently hydrogen, cyano, nitro, trifluoromethoxy, trifluoromethyl, or alkylsulfonyl are antagonists of at least one tachykinin receptor and are useful in the treatment of depression, anxiety, asthma, pain, inflammation, urinary incontinence and other disease conditions. Process for their preparation are described, as are compositions containing them and their use.
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- Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material
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Vignafuran 2, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester 3, and coumestrol 4 were efficiently synthesized from the same starting material, 4-bromoresorcinol 14a, through the common intermediate, diarylacetylene 7. The key steps of these syntheses were the tetrabutylammonium fluoride (TBAF)-catalyzed benzo[b]furan ring formation for 2 and the carbonylative ring closure methodology catalyzed by a Pd complex for 3 and 4. The Royal Society of Chemistry 2000.
- Hiroya, Kou,Suzuki, Naoyuki,Yasuhara, Akito,Egawa, Yuya,Kasano, Atsushi,Sakamoto, Takao
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p. 4339 - 4346
(2007/10/03)
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- Phenol compound having antioxidative activity and the process for preparing the same
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Disclosed are a phenol compound represented by the formula (1): STR1 wherein R0 represents H, alkyl or alkyloxy; R1 represents alkyl; R2 represents alkyl or alkyloxy; OR3 represents OH; R4 represents H, lower alkyl or acyl, each of the above substituents may be substituted; W represents O, S or NR7 ; where R7 represents H, alkyl, aryl, OH or alkyloxy, a group of the formula (2): STR2 represents an amino which may be mono- or di-substituted or heterocyclic group containing N atom, or a pharmaceutically acceptable salt thereof, and a process for preparing the same.
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- N-Bromosuccinimide as a Regioselective Nuclear Monobrominating Reagent for Phenols and Naphthols
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A wide range of substituted phenols and naphthols were regioselectively monobrominated with N-bromosuccinimide, at para position in acetonitrile and at ortho position in carbon disulfide, under mild conditions in good yields. Methylphenols afforded only nuclear bromination products.
- Carre?o, M. Carmen,García Ruano, José L.,Sanz, Gema,Toledo, Miguel A.,Urbano, Antonio
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p. 1241 - 1242
(2007/10/03)
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- Syntheses of the Natural Dibenzofuran, Ruscodibenzofuran
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Short syntheses of the natural dibenzofuran, ruscodibenzofuran (1) from readily available phenols are described.The key step involve initial formation of a 2-isopropenylbenzofuran by reaction of an ortho-halogenophenol with cuprous isopropenylacetylide fo
- Scannell, Ralph T.,Stevenson, Robert
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p. 2927 - 2932
(2007/10/02)
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