- Rhodium(I)-Catalyzed Three-Component [4+2+1] Cycloaddition of Two Vinylallenes and CO
-
Transition metal-catalyzed [4+2+1] reactions of dienes (or diene derivatives such as vinylallenes), alkynes/alkenes, and CO (or carbenes) are expected to be the most straightforward approach to synthesize challenging seven-membered ring compounds, but so far only limited successes have been realized. Here, an unexpected three-component [4+2+1] reaction between two vinylallenes and CO was discovered to give highly functionalized tropone derivatives under mild conditions, where one vinylallene acts as a C4 synthon, the other vinylallene as a C2 synthon, and CO as a C1 synthon. It was proposed that this reaction occurred via oxidative cyclization of the diene part of one vinylallene molecule, followed by insertion of the terminal alkene part of the allene moiety in another vinylallene, into the Rh?C bond of five-membered rhodacycle. Then, CO insertion and reductive elimination gave the [4+2+1] cycloadduct. Further experimental exploration of why ene/yne-vinylallenes and CO gave monocyclic tropone derivatives instead of 6/7-bicyclic ring products were reported here.
- Cui, Qi,Tian, Zi-You,Yu, Zhi-Xiang
-
supporting information
p. 5638 - 5641
(2021/03/06)
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- Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases
-
The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.
- González-Granda, Sergio,Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor-Fernández, Vicente
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p. 520 - 527
(2019/11/16)
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- Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
-
A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.
- Breit, Bernhard,Schmidt, Johannes P.
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p. 23485 - 23490
(2020/10/29)
-
- A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles
-
A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.
- Ieronimo, Gabriella,Palmisano, Giovanni,Maspero, Angelo,Marzorati, Alessandro,Scapinello, Luca,Masciocchi, Norberto,Cravotto, Giancarlo,Barge, Alessandro,Simonetti, Marco,Ameta, Keshav Lalit,Nicholas, Kenneth M.,Penoni, Andrea
-
supporting information
p. 6853 - 6859
(2018/10/20)
-
- Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes
-
The development of a gold(III) catalyzed direct enantioconvergent 1,5-enyne cycloisomerization and kinetic resolution reaction is described. The transformation results in highly enantioenriched bicyclo[3.1.0]hexenes at all levels of conversion, with no racemization or symmetrization taking place during the course of the reaction, and simultaneously affords optically enriched 1,5-enynes. This report marks the first highly enantioselective transformation catalyzed by a well-defined cationic gold(III) catalyst and demonstrates the unique potential of gold(III) complexes in enantioselective catalysis.
- Bohan, Patrick T.,Dean Toste
-
supporting information
p. 11016 - 11019
(2017/08/22)
-
- Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel-Crafts alkylation and dehydration to tricyclic benzo[f] isochromenes
-
A three-step domino reaction between 1-aryl-3-hexyne-2,6-diol derivatives and aldehydes is used to construct tricyclic 1,4-dihydro-2H-benzo[f]isochromenes. The cascade is initiated by BF3·OEt2 and involves alkynyl-Prins cyclization, Friedel-Crafts alkenylation, and dehydration/aromatization to create a new, central aromatic ring and eliminate 2 equiv. of water. Electron-donating substituents on the aryl ring of the 1-aryl-3-hexyne-2,6-diols significantly increase overall yields as do electron-rich aldehyde reaction partners. For 2,4-disubstituted 2H-benzo[f]isochromene products, diastereoselectivities in the alkynyl-Prins reaction are ~1.4:1 in favor of the cis-diastereomer. The stereochemistry of one cis-product was verified by X-ray crystallographic analysis and a second structure was also verified by X-ray analysis.
- Hinkle, Robert J.,Chen, Yuzhou,Nofi, Colleen P.,Lewis, Shane E.
-
supporting information
p. 7584 - 7593
(2017/09/27)
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- Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach
-
A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.
- Li, Wenhua,Lin, Zuming,Chen, Long,Tian, Xuechao,Wang, Yan,Huang, Sha-Hua,Hong, Ran
-
supporting information
p. 603 - 606
(2016/01/20)
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- Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols
-
Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.
- Yun, Jihee,Park, Jungmin,Kim, Jaehyun,Lee, Kooyeon
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p. 1045 - 1048
(2015/02/19)
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- Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex
-
A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without
- Cheng, Li-Jie,Cordier, Christopher J.
-
supporting information
p. 13734 - 13738
(2015/11/11)
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- Stereocontrol in palladium-catalyzed propargylic substitutions: Kinetic resolution to give enantioenriched 1,5-enynes and propargyl acetates
-
Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily
- Ardolino, Michael J.,Eno, Meredith S.,Morken, James P.
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supporting information
p. 3413 - 3419
(2013/12/04)
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- Kinetic resolution of propargylic alcohols via stereoselective acylation catalyzed by lipase PS-30
-
By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic propargylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 139. Substituent effect is briefly discussed.
- Chen, Peiran,Zhu, Xiyin
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p. 184 - 188
(2013/10/01)
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- New and efficient synthesis of 1,3-dienylphosphonates by palladium-catalyzed substitution of propargylic esters to diethyl phosphite
-
An efficient route to the synthesis of 1,3-dienylphosphonates (1) has been developed for the first time by the substitution of propargylic esters (2) to the diethyl phosphite (3) nucleophile in the presence of Pd2 (dba) 3 · CHCl3 (2 mol %) and 2,2′- bis(diphenylphosphino)-1,1′-binaphthyl (4 mol%). Both the alkyl and aryl 1,3-dienylphosphonates can be prepared from this transformation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Liu, Xiao-Ning,Guo, Wei-Lei,Hou, Chuan-Jin,Hu, Xiang-Ping
-
supporting information
p. 2622 - 2626
(2013/07/26)
-
- SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ, NR1F3)
-
The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administration of these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof as well as pharmaceutical compositions comprising said compounds as an active ingredient.
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-
Page/Page column 59
(2013/05/22)
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- Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)
-
The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.
- Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
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p. 11824 - 11834
(2014/01/06)
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- Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols
-
A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.
- Wang, Yan,Zheng, Kuan,Hong, Ran
-
supporting information; scheme or table
p. 4096 - 4099
(2012/04/10)
-
- Synthesis of allenes via gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds
-
Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.
- Xu, Cheng-Fu,Xu, Mei,Yang, Liu-Qing,Li, Chuan-Ying
-
experimental part
p. 3010 - 3016
(2012/05/05)
-
- Enantioselective copper-catalysed propargylic substitution: Synthetic scope study and application in formal total syntheses of (+)-anisomycin and (-)-cytoxazone
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A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone. Copyright
- Detz, Remko J.,Abiri, Zohar,Le Griel, Remi,Hiemstra, Henk,Van Maarseveen, Jan H.
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experimental part
p. 5921 - 5930
(2011/06/26)
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- An efficient approach to 2-bromoalken-3-ols by regioselective bromohydroxylation reaction of simple allenes with NBS
-
A regioselective bromohydroxylation reaction of simple allenes affording 2-bromoalken-3-ols in moderate-to-good yields has been developed by using NBS as the electrophilic reagent in a mixture of 1,4-dioxane/H2O (1:1) at room temperature. Throu
- Kong, Wangqing,Guo, Binjie,Fu, Chunling,Ma, Shengming
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p. 2278 - 2285
(2011/06/19)
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- Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B
-
A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.
- Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
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supporting information; experimental part
p. 500 - 511
(2011/04/17)
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- N-Vinylpyridinium tetrafluoroborate salts as reagents for the stereoselective and regioselective synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes
-
We had previously demonstrated the utility of N-vinylpyridinium tetrafluoroborate salts as novel electrophilic coupling partners in Pd(0)-catalyzed Suzuki cross-coupling reactions with aryl and vinyl boronic acids. We now report that these crystalline, air-stable, and non-hygroscopic salts are also useful reagents for the synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes (diene diones), which in turn are valuable starting materials for the synthesis of various five-membered heterocycles. The optimization of reaction conditions and the scope and limitations of the reductive dimerization are discussed.
- Gao, Ge,Brown, Neil,Minatoya, Machiko,Buszek, Keith R.
-
scheme or table
p. 6491 - 6494
(2009/04/06)
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- Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols
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(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.
- Cheng, Xin,Jiang, Xuefeng,Yu, Yihua,Ma, Shengming
-
scheme or table
p. 8960 - 8965
(2009/04/11)
-
- Synthesis of pyridazine-based scaffolds as α-helix mimetics
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The synthesis of several amphiphilic, nonpeptidic scaffolds that mimic the presentation of i, i + 3 or i + 4, and i + 7 residues of a peptide α-helix is described. The approach uses a pyridazine core, and the synthesis involves only a few steps and minimi
- Volonterio, Alessandro,Moisan, Lionel,Rebek Jr., Julius
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p. 3733 - 3736
(2008/02/12)
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- Syntheses and synthetic applications of stannylated allylic alcohols
-
Allenyl carbinols undergo regioselective hydrostannation in the presence of MoBl3, a catalyst originally developed for the hydrostannation of alkynes, giving rise to allyl stannanes. These allyl stannanes can easily be converted into useful synthetic building blocks such as allyl iodides or vinyl epoxides.
- Kazmaier, Uli,Lucas, Simon,Klein, Manuela
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p. 2429 - 2433
(2007/10/03)
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- Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes
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A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by IC1, I 2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.
- Zhang, Xiaoxia,Sarkar, Sampa,Larock, Richard C.
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p. 236 - 243
(2007/10/03)
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- Synthesis of azide-alkyne fragments for 'click' chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols
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A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazole-based peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery.
- Montagnat, Oliver D.,Lessene, Guillaume,Hughes, Andrew B.
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p. 6971 - 6974
(2007/10/03)
-
- Enantiocontrolled synthesis of 3-pyrrolines from α-amino allenes
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Cyclization of α-amino allenes in the presence of N-bromosuccinimide afforded pyrrolines in good yields. The products were obtained with high enantiomeric excesses when optically active allenes were used as substrates. The synthesis of a 2,5-dehydroprolinol derivative is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Horvath, Attila,Benner, Jessica,Baeckvall, Jan-E.
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p. 3240 - 3243
(2007/10/03)
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- Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift
-
Treatment of benzyl γ-(trimethylsilyl)propargyl ether with n-BuLi is shown to afford the rarely precedent ortho-[2,3]-Wittig product in remarkable preference to the [1,2]-Wittig product. The factors governing the periselectivity in this type of carbanion
- Tomooka, Katsuhiko,Harada, Manabu,Hanji, Takayuki,Nakai, Takeshi
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p. 1394 - 1395
(2007/10/03)
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- Facile preparation of substituted allenic esters via the ortho ester Claisen rearrangement
-
Five substituted allenic esters were prepared in good yields through the ortho ester Claisen rearrangement of primary and secondary propargyl alcohols.
- Lai,Anderson
-
p. 4087 - 4091
(2007/10/03)
-
- Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.
-
Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of β-hydroxy-α-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of γ-hydroxy-α,β-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
- Burgess, Kevin,Jennings, Lee D.
-
p. 6129 - 6139
(2007/10/02)
-
- Novel 6-alkyl and 6.8-dialkylbicyclo(4.2.0)octane derivatives
-
Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): STR1 wherein: A is --C C--, trans --HC=CH--, trans --CH=CHCH2 -- or --CH2 CH2 --; X is lower alkyl of 1-6 carbon atoms; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer from 2-4; R1 is --CH2 OH, --CHO, --CO2 R or --CO2 H, and the olefin formed by the R1 (CH2)n CH= moiety is either (E) or (Z); R2 is hydrogen or methyl, or optionally --CH=CH2 when A is trans --CH=CHCH2 --; and R3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, STR2 --(CH2)m -phenyl or CH2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen. in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is STR3 wherein X' is STR4 in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, or a pharmaceutically acceptable, non-toxic salt or ester thereof.
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-
-
- Novel substituted (4.2.0)bicyclooctane derivatives with valuable therapeutic properties
-
Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): STR1 wherein: A is --C C--, trans --HC=CH--, --CH2 CH2 -- or --CH=CHCH2 --; X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); is an integer of 2-4; R1 is --CH2 OH, --CHO, --CO2 R or --CO2 H, and the olefin formed by the R1 (CH2)n CH= moiety is either (E) or (Z); R2 is hydrogen or methyl, or optionally --CH=CH2 when A is --CH=CHCH2 --; and R3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, STR2 --(CH2)m -phenyl or CH2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen; in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is STR3 wherein x is STR4 in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.
- -
-
-
- Novel 8-(lower alkyl)bicyclo[4.2.0]octane derivatives with valuable therapeutic properties
-
Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): STR1 wherein: Y is exo-(lower alkyl) or endo-(lower alkyl); n is 2 or 3; R1 is CH2 OH, CHO, CO2 R or CO2 H; R2 is hydrogen or methyl; and R3 is linear or branched alkyl having 5-10 carbon atoms, STR2 or --(CH2)m -phenyl optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, in which a is 0, 1 or 2; b is 3-7; m is 1 or 2; and R is STR3 wherein X is STR4 in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.
- -
-
-
- Novel [4,2,0]bicyclooctane derivatives with valuable therapeutic properties
-
Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): STR1 wherein: n is 2 or 3; R1 is CH2 OH, CHO, CO2 R or CO2 H; R2 is hydrogen or methyl; and R3 is linear or branched alkyl having 5-10 carbon atoms, STR2 optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, in which a is 0, 1 or 2; b is 3-7; m is 1 or 2; and R is STR3 in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.
- -
-
-
- The Synthesis of 9-Substituted N-Benzyl-8-azabicyclonon-4-en-7-ones by the Intramolecular Diels-Alder Reaction
-
The intramolecular thermal cyclisation of N-allyl-N-benzylpenta-2(E),4-dienamide in refluxing NN-dimethylformamide gives N-benzyl-cis- and trans-8-azabicyclonon-4-en-7-one; N-allyl-N-benzylhexa-2(E),4(E)-dienamide gives (1RS, 3RS, 6SR)-3-methyl- an
- Brettle, Roger,Jafri, Iftikhar A.
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p. 387 - 394
(2007/10/02)
-