- Discovery of the PARP (poly ADP-ribose polymerase) inhibitor 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide for the treatment of cancer
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In this work, two series of cyclic amine-containing benzimidazole carboxamide derivatives were designed and synthesized as potent anticancer agents. PARP1/2 inhibitory activity assays indicated that most of the compounds showed significant activity. The in vitro antiproliferative activity of these compounds was investigated against four human cancer cell lines (MDA-MB-436, MDA-MB-231, MCF-7 and CAPAN-1), and several compounds exhibited strong cytotoxicity to tumor cells. Among them, 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide (17d) was found to be effective PARP1/2 inhibitors (IC50 = 4.30 and 1.58 nM, respectively). In addition, 17d possessed obvious selective antineoplastic activity and noteworthy microsomal metabolic stability. What's more, further studies revealed that 17d was endowed with an excellent ADME profile. These combined results indicated that 17d could be a promising candidate for the treatment of cancer.
- Chen, Dawei,Jiang, Yuyang,Shi, Zhichao,Tang, Lin,Wu, Weibin,Zhai, Xin,Zhang, Cunlong
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-
- Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes
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A methodology for the synthesis of 7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocines from aromatic aldehydes and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine using catalysis by trifluoroacetic and perchloric acids is described. The developed protocol was applied for the synthesis of N-unsubstituted and N-methyl-4-aryltetrahydroisoquinolines.
- Buev, Evgeny M.,Stepanov, Maxim A.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
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supporting information
p. 631 - 635
(2020/01/31)
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- Discovery of 2-(1-(3-(4-Chloroxyphenyl)-3-oxo-propyl)pyrrolidine-3-yl)-1H-benzo[d]imidazole-4-carboxamide: A Potent Poly(ADP-ribose) Polymerase (PARP) Inhibitor for Treatment of Cancer
-
A series of benzimidazole carboxamide derivatives have been synthesized and characterized by 1H-NMR, 13C-NMR and HRMS. PARP inhibition assays and cellular proliferation assays have also been carried out. Compounds 5cj and 5cp exhibited potential anticancer activities with IC50 values of about 4 nM against both PARP-1 and PARP-2, similar to the reference drug veliparib. The two compounds also displayed slightly better in vitro cytotoxicities against MDA-MB-436 and CAPAN-1 cell lines than veliparib and olaparib, with values of 17.4 μM and 11.4 μM, 19.8 μM and 15.5 μM, respectively. The structure-activity relationship based on molecular docking was discussed as well.
- Min, Rui,Wu, Weibin,Wang, Mingzhong,Tang, Lin,Chen, Dawei,Zhao, Huan,Zhang, Cunlong,Jiang, Yuyang
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- A fluorine-containing substituted benzimidazole derivative and application thereof (by machine translation)
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The invention belongs to the field of medicinal chemistry, relates to a fluorine-containing substituted benzimidazole derivative and application thereof. The substituted benzimidazole derivatives of formula I compounds are shown, or its tautomer, enantiomer, non-enantiomer, racemate in, racemate or a mixture thereof, or its prodrug, or their pharmaceutically acceptable salt, solvate or hydrate. It can be used for treating upper effective PARP inhibitors, for the prevention and treatment of diseases related to the PARP. (by machine translation)
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- With antifungal activity of the wicked zuozuo apperception compound and its preparation method and application (by machine translation)
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The invention discloses an oxazole compound with anti-fungal activity, a preparation method of the oxazole compound and an application of the oxazole compound to tobacco powdery mildew original fungi or cotton anthracnose original fungi prevention, and belongs to the technical field of organic synthesis. The technical scheme mainly includes that the oxazole compound with the anti-fungal activity is provided with a structure shown in the instruction, R1 refers to propiono, isopropyl, acetyl, ethyl or methyl, and R2 refers to dimethylamino or methylamine. Five oxazole compounds with the anti-fungal activity are synthesized by the novel method, the preparation process is simple in technology and easy to control, target product yield is high, repeatability is fine, and the five prepared oxazole compounds with the anti-fungal activity have a certain prevention function for tobacco powdery mildew original fungi or cotton anthracnose original fungi.
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- Bronsted acid or lewis acid catalyzed [3+3] cycloaddition of azomethine imines with N-benzyl azomethine ylide: A facile access to bicyclic N-heterocycles
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1,3-Dipolar cycloaddition reactions are one of the most important methods to obtain diverse heterocycles with novel skeletons. We herein report the Bronsted acid or Lewis acid catalyzed [3+3] cycloaddition of azomethine imines with nonstabilized azomethine ylide generated in situ from an N-benzyl precursor, providing a clean and facile access to diverse bicyclic N-heterocycles in moderate to good yields for further biological testing. Also, the protocol developed achieved the formation of C-C and C-N bonds simultaneously in a single step.
- Li, Shuo-Ning,Yu, Bin,Liu, Jia,Li, Hong-Lian,Na, Risong
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p. 282 - 286
(2016/01/20)
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- Stereo-, Regio-, and Chemoselective [3 + 2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study
-
One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclic compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields. The structures of the products were established by spectroscopic techniques as well as by single-crystal XRD study, and DFT calculations were performed to further understand the mechanism of this [3 + 2]-cycloaddition reaction.
- Sankar, Ulaganathan,Surya Kumar, Ch. Venkata,Subramanian,Balasubramanian,Mahalakshimi
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p. 2340 - 2354
(2016/04/04)
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- (3,4-DICHLORO-PHENYL)-((S)-3-PROPYL-PYRROLIDIN-3-YL)-METHANONE HYDROCHLORIDE AND MANUFACTURING PROCESSES
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The present invention is concerned with a novel process for the preparation of a compound of formula I and its hydrates The compounds of formula I and the corresponding hydrates are pharmaceutically active substances.
- -
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Paragraph 0434-0435
(2015/02/25)
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- PYRAZOLO[4,3-D]PYRIMIDIN-7(6H)-ONE DERIVATIVES AS PDE9 INHIBITORS
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Pyrazolo[4,3-d]pyrimidin-7(6H)-one derivatives represented by the general formula (I), wherein R1 represents hydrogen atom or methyl; when R1 represents hydrogen atom, then R2 represents cyclopentyl, tetrahydropyranyl, cyclohexyl, or cyclohexyl substituted with 1 or 2 halogen atoms; when R1 represents methyl, then R2 represents cyclopentyl; R3 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, and OCH3; and 6- to 10-membered heteroaryl with 1 to 3 heteroatoms selected independently form O, N and S; and Q represents C1-C3-alkylene group, which is unsubstituted or substituted with 1 to 3 C1-C3-alkyl groups; and their salts. The compounds are PDE9A inhibitors useful as m edicaments, in particular for treatment of cognitive function disorders and neurodegenerative diseases
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Page/Page column 24-25
(2014/03/21)
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- SPIROCYCLIC DERIVATIVES AS ANTIPARASITIC AGENTS
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The invention recites spirocyclic derivatives of Formula (V.1) or (V.2), stereoisomers thereof, veterinary acceptable salts thereof, compositions thereof, processes for making, and their use as a parasiticide for an animal. The variables A, B, V, Z, Y, W1, W2, W3, R1a, R1b, R1c, R2, R3, R4, n, and "---" are as described herein.
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- Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetrakis(pentafluorophenyl)porphyrin: A study using 1,3-dipolar cycloadditions under mild conditions
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The 1,3-dipolar cycloaddition of meso-tetrakis(pentafluorophenyl)porphyrin and its nickel complex, with the bulky azomethine ylide dipole was studied under mild conditions, and yielded chlorin and isobacteriochlorin derivatives self-prevented from aggregation. The reactions were performed at room temperature or 0 C, and we were able to establish a set of reaction conditions to obtain only the chlorin or the isobacteriochlorin. These compounds were evaluated in solution, and no aggregation was observed at less than 25 mM (~30 mg mL-1) using 1H NMR experiments.
- De Souza, Juliana M.,De Assis, Francisco F.,Carvalho, Carla M.B.,Cavaleiro, José A.S.,Brocksom, Timothy J.,De Oliveira, Kleber T.
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supporting information
p. 1491 - 1495
(2014/03/21)
-
- (3,4-DICHLORO-PHENYL)-((S)-3-PROPYL-PYRROLIDIN-3-YL)-METHANONE HYDROCHLORIDE AND MANUFACTURING PROCESSES
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The present invention is concerned with a novel process for the preparation of a compound of formula I and its hydrates, as well as with a crystall polymorph thereof. The compounds of formula (I) and the corresponding hydrates are pharmaceutically active substances.
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Page/Page column 91
(2013/11/18)
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- Design, synthesis, and validation of a β-turn mimetic library targeting protein - Protein and peptide - Receptor interactions
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The design and synthesis of a β-turn mimetic library as a key component of a small-molecule library targeting the major recognition motifs involved in protein - protein interactions is described. Analysis of a geometric characterization of 10?245 β-turns in the protein data bank (PDB) suggested that trans-pyrrolidine-3,4-dicarboxamide could serve as an effective and synthetically accessible library template. This was confirmed by initially screening select compounds against a series of peptide-activated GPCRs that recognize a β-turn structure in their endogenous ligands. This validation study was highlighted by identification of both nonbasic and basic small molecules with high affinities Ki = 390 and 23 nM, respectively) for the ?-opioid receptor (KOR). Consistent with the screening capabilities of collaborators and following the design validation, the complete library was assembled as 210 mixtures of 20 compounds, providing a total of 4200 compounds designed to mimic all possible permutations of 3 of the 4 residues in a naturally occurring β-turn. Unique to the design and because of the C 2 symmetry of the template, a typical 20 × 20 × 20-mix (8000 compounds prepared as 400 mixtures of 20 compounds) needed to represent 20 variations in the side chains of three amino acid residues reduces to a 210 × 20-mix, thereby simplifying the library synthesis and subsequent screening. The library was prepared using a solution-phase synthetic protocol with liquid - liquid or liquid - solid extractions for purification and conducted on a scale that insures its long-term availability for screening campaigns. Screening the library against the human opioid receptors (KOR, MOR, and DOR) identified not only the activity of library members expected to mimic the opioid receptor peptide ligands but also additional side-chain combinations that provided enhanced receptor binding selectivities (>100-fold) and affinities (as low as Ki = 80 nM for KOR). A key insight to emerge from the studies is that the phenol of Tyr in endogenous ligands bearing the H-Tyr-Pro-Trp/Phe-Phe-NH2 β-turn is important for MOR binding but may not be important for KOR (accommodated, but not preferred) and that the resulting selectivity for KOR observed with its removal can be increased by replacing the phenol OH with a chlorine substituent, further enhancing KOR affinity.
- Whitby, Landon R.,Ando, Yoshio,Setola, Vincent,Vogt, Peter K.,Roth, Bryan L.,Boger, Dale L.
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p. 10184 - 10194
(2011/09/12)
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- Small molecule peptidomimetic inhibitors of importin α/β mediated nuclear transport
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Nucleocytoplasmic transport of macromolecules is a fundamental process of eukaryotic cells. Translocation of proteins and many RNAs between the nucleus and cytoplasm is carried out by shuttling receptors of the β-karyopherin family, also called importins and exportins. Leptomycin B, a small molecule inhibitor of the exportin CRM1, has proved to be an invaluable tool for cell biologists, but up to now no small molecule inhibitors of nuclear import have been described. We devised a microtiter plate based permeabilized cell screen for small molecule inhibitors of the importin α/β pathway. By analyzing peptidomimetic libraries, we identified β-turn and α-helix peptidomimetic compounds that selectively inhibit nuclear import by importin α/β but not by transportin. Structure-activity relationship analysis showed that large aromatic residues and/or a histidine side chain are required for effective import inhibition by these compounds. Our validated inhibitors can be useful for in vitro studies of nuclear import, and can also provide a framework for synthesis of higher potency nuclear import inhibitors.
- Ambrus, Géza,Whitby, Landon R.,Singer, Eric L.,Trott, Oleg,Choi, Euna,Olson, Arthur J.,Boger, Dale L.,Gerace, Larry
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supporting information; scheme or table
p. 7611 - 7620
(2011/02/21)
-
- Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
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Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Δ-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin, anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright
- Thaqi, Ali,Scott, Janet L.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
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supporting information; experimental part
p. 1717 - 1723
(2010/07/02)
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- Small molecule inhibitors of Myc/Max dimerization and Myc-induced cell transformation
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The preparation and evaluation of a series of inhibitors of Myc/Max dimerization and Myc-induced cell transformation are described providing mycmycin-1 (3) and mycmycin-2 (4).
- Shi, Jin,Stover, James S.,Whitby, Landon R.,Vogt, Peter K.,Boger, Dale L.
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scheme or table
p. 6038 - 6041
(2010/04/05)
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- Process For Preparing Alkyl(Methoxymethyl)Trimethylsilanylmethylamines
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Alkyl(methoxymethyl)trimethylsilanylmethylamines are prepared by reacting alkyltrimethylsilanylmethylamines with a substantially equimolar amount of paraformaldehyde and methanol in the presence of a base.
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Page/Page column 3-4; 4
(2009/04/24)
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- ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS
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Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of MC-4R, such as obesity, diabetes, nicotine addiction, alcoholism, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.
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Page/Page column 85
(2008/06/13)
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- Synthesis of 3-substituted pyrrolidines
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A method was developed for the synthesis of derivatives of 3-substituted pyrrolidines from activated alkenes by 1,3-dipolar cycloaddition of unstable 2-benzylazomethylide, generated in situ from N-benzyl-N-(methoxymethyl)-N- (trimethylsilyl)amine. A method was developed for the reduction of 4-(3-pyrrolidyl)pyridine, prepared by the above-mentioned method, to the corresponding derivatives of (3-pyrrolidyl)piperidine with high yields under mild conditions.
- Kurkin,Sumtsova,Yurovskaya
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- 1, 2, 3, 3A, 8, 8A-HEXAHYDRO-2, 7A-DIADA-CYCLOPENTA [A] INDEN-7-ONE DERIVATIVES WHICH BIND TO NEURONAL NICOTINIC ACETYLCHOLINE SPECIFIC RECEPTOR SITES AND ARE USEFUL IN MODULATING CHOLINERGIC FUNCTION AND IN THE TREATMENT OF ADDICTIVE DISORDERS
-
The present invention relates to novel fused bicyclicpyrrolidine pyridone compounds of the formula (I) wherein R, RP and n are as defined herein, their pharmaceutically acceptable salts, pharmaceutical compositions and their use in treating addictive disorders such as the use of tobacco or other nicotine containing products and in the treatment of neurological and mental disorders related to a decrease in cholinergic function.
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Page/Page column 17
(2008/06/13)
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- Process for the preparation of substituted pyrrolidine derivatives and intermediates
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Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.
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Page/Page column 7
(2010/11/08)
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- Novel benzothiazole compounds and methods of use thereof
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The present invention relates to methods of preparing compounds having formula (1), (2), (5), and ((6A)-(6D)) comprising contacting the corresponding ester, an amine with formula NHR1R2, and a Lewis acid having formula MLn, wherein L is a halogen atom or an organic radical, n is 3-5, and M is a group III elemental atom, a group IV elemental atom, As, Sb, V or Fe, wherein A, B, V, X, Z, W, R1, R2, R5, Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are substituents. Z4, Z5, Z6, Z7, and Z8 are substituents.
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Page/Page column 6; 13
(2010/10/20)
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- A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition
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(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.
- Kotian, Pravin L.,Lin, Tsu-Hsing,El-Kattan, Yahya,Chand, Pooran
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p. 193 - 197
(2012/12/24)
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- AMIDINOPHENYL-PYRROLIDINES, -PYRROLINES, AND -ISOXAZOLIDINES AND DERIVATIVES THEREOF
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The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula (I), or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(=NH)NH2 and the other H and J and J may be O or CH2, which are useful as inhibitors of factor Xa.
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- Branched alkyl pyrrolidine-3-carboxylic acids
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Branched alkyl pyrrolidines of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropatnological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
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- Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof
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The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(=NH)NH2 and the other H, and J1 and J2 may be O or CH2, which are useful as inhibitors of factor Xa.
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-
- Non-stabilized azomethine ylides in [3 + 2] cycloadditions. Pyrrolidinylfuranones from (5S)-5-menthyloxy-4-vinylfuran-2(5H)-one
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Upon sonication with lithium fluoride in acetonitrile N-benzyl-N-methoxymethyl(trimethylsilylmethyl)amines 9a-c undergo chemoselective 1,3-dipolar cycloaddition with 4-vinylfuranones 2 and 6 to afford pyrrolidinylfuranones 10, 11a-c and 12a-c. The stereochemistry is assigned by X-ray analyses and proton NMR data comparison of related oxiranylfuranone 13.
- Gerlach, Kai,Hoffmann,Wartchow
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p. 3867 - 3872
(2007/10/03)
-
- Single and double diastereoselection in azomethine ylide cycloaddition reactions with unsaturated chiral bicyclic lactams
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Double diastereoselectivity data were analyzed to provide insight into the structural features that influence π-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (ΔΔG(≠)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R2) and concave faces of the bicyclic lactams. This effectively hindered both α- and β-approaches in the nonextended transition states. The second major steric interaction was provided by the nonbonded interactions (i) between the R1 angular substituent on the bicyclic lactam and the π-system of the dipole. This interaction was shown to be very significant, causing reversal in π-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.
- Fray,Meyers
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p. 3362 - 3374
(2007/10/03)
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- On the Use of N-amino Ethers as Capped Azomethine Ylide Equivalents
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N-amino ethers have been found to act as azomethine ylide equivalents.Treatment of these compounds with lithium fluoride in the presence of a reactive dipolarophile afforded dipolar cycloadducts in high yield.The cycloaddition proceeded with complete stereospecificity with dimethyl fumarate and maleate.This result is consistent with the intermediacy of an azomethine ylide.The reaction of N-benzyl-N-(methoxymethyl)-N-amine afforded several silylated diamines when treated with zinc chloride or cesium fluoride in the absence of trapping agent.This can be attributed to an initial loss of the methoxy group to give a transient iminium ion.This species reacts further with the azomethine ylide or undergoes hydrolysis to give a silylated amine.The cycloaddition behavior of several unsymmetrically substituted azomethine ylide precursors was also examined.Competitive rate studies showed that the cycloaddition is compatible with a HOMO-controlled process.The regiochemistry of the cycloaddition, however, is not easily rationalized by simple FMO considerations and may instead be related to the charge transfer interaction energy of the reaction.
- Padwa, Albert,Dent, William
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p. 235 - 244
(2007/10/02)
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- Trifluoroacetic Acid-Catalyzed 1,3-Cycloaddition of the Simplest Iminium Ylide Leading to 3- or 3,4-Substituted Pyrrolidines and 2,5-Dihydropyrroles
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The 1,3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3- or 3,4-substituted pyrrolidines and 2,5-dihydropyrroles.
- Terao, Yoshiyasu,Kotaki, Hiromi,Imai, Nobuyuki,Achiwa, Kazuo
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p. 2762 - 2766
(2007/10/02)
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- N-(TRIMETHYLSILYLMETHYL)AMINOMETHYL ETHERS AS AZOMETHINE YLIDE SYNTHONS. A NEW AND CONVENIENT ACCESS TO PYRROLIDINE DERIVATIVES
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The title compounds, readily prepared from (trimethylsilylmethyl)amines, formaldehyde and an alcohol, react with electron deficient alkenes in the presence of iodosilane or silyl triflate in combination with cesium fluoride to give the corresponding pyrrolidine derivatives stereospecifically in excellent yield.
- Hosomi, Akira,Sakata, Yasuyuki,Sakurai, Hideki
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p. 1117 - 1120
(2007/10/02)
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