Miniaturized microreactors enable photochemistry with laser irradiation in flow mode to convert azidobiphenyl into carbazole with high efficiency

Avemaria, Frank

Bremus-Köbberling, Elke Auguste

Bräse, Stefan

Gillner, Arnold

Réthoré, Céline

Beilstein Journal of Organic Chemistry

English

PubMed

RWTH Publications

Photochemistry with laser radiation in condensed phase using miniaturized photoreactors

Shatokhin, O.

eLibrary National Mining University

Shatokhin O. National Metallurgical Academy of Ukraine  MANAGEMENT DECISION MAKING IN MARKETING  Theoretical bases of management decision making in marketing, that rapid growth now in the western theory and practice of management, must be adapted to the crisis conditions of Ukraine and widely utillized in domestic science and economic activity of the Ukrainian commercial firms.  Marketing purpose is to define needs and demands of consumers, to set the system of consumer favors (their preferences, what they turn attention at the first, etc.), to find out where and when users purchase products, how they get information about its advantages and even about existence (to define what forms and methods of advancement of commodities and services are better at the market), why users prefer your goods than other’s ones. Therefore concept, "marketing" in wide sense is not limited to studying only consumer’s demand, but also tells how to promote new products at the market. The process of management marketing is complicated and many-sided, he foresees the selection of such important categories as functions. In functions a management opens up nature and maintenance of administrative activity on all of levels of management an enterprise.    Management functions are relatively separate kinds and directions of administrative activity, which are characterized complete homogeneity, complication and stability.  They help to carry out purposeful influence on object and subject management with the purpose of meeting a goal objective in concrete terms socio-economic processes.  A management should be considered as a cyclic process, which consists of concrete types of administrative works, urgent management functions. Management functions are a concrete types of administration, that is performed using the special receptions and methods, and also proper organization of work and quality assurance. As evidently, one of basic components which make maintenance of management are functions. So we need to know the goal we should achieve, we need to know how to organize activity, how to motivate and control its implementation. Management functions have specifity. They can be operated as separate or dependent entities or even they can be part of other one. For example, information, collected by implementation of control function, "tells" managers, as their plans are fulfiled (planning function). At the same time control must be proper a rank explained and organized (function of motivation and organization). In other words, in control the system all of administrative functions are united in the unique integral process. If a manager wishes to provide the "bright future" of the company, he should carry out all of administrative functions constantly. And he  should begin from planning. If is planned, it should be and organized, and workers geared-up for its implementation.  Quality of working process in a large measure depends on propulsive reasons, offered a manager. To define exactness of fulfiling the plans, it is needed to control the working process.  Thus, management functions can be presented as types of administrative labour, related to administrated object. In the management process the followings basic functions are executed: planning, organization, motivation and control.  Each of four functions of management is a very important for company. At the same time planning as management function provides basis for other functions and considered the most important from them, the functions of organization, motivation and control, are oriented to fulfiling the tactical and strategic plans of organization. It follows to underline that sphere of knowledges about a management marketing in everyday marketing activity directly related to the questions of management economic relationship. In other words, in economic activity it is extraordinarily difficult to define actually an administrative decision from a decision which carries marketing character.  And although in a theoretical plan this difference is fixed, in actual fact every decision realizes some mechanisms of adjusting of market relations which are the article of marketing theory.   In the field of management directly a management marketing comes forward as motivation of labour of step of enterprise, estimation of economic decisions, strategic planning, choice of form of ménage, structure of management, management a personnel, imitation design et al.  Base principle of marketing on an enterprise is an exposure of market necessities, development and realization of marketing’s strategies, providing of satisfaction of these necessities, is at more high-quality level, than for competitors. In the conditions of continuously variable market environment an enterprise keeps the positions offers new commodities, promotes quality and range of goods and services, provides an effective informative exchange with users by sales promotion.  

MANAGEMENT DECISION MAKING IN MARKETING

Elke Bremus-Köbberling

Arnold Gillner

Frank Avemaria

Céline Réthoré

Stefan Bräse

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Publikationsserver der RWTH Aachen University

Bremus-Köbberling, E.

Gillner, A.

Avemaria, F.

Rethore, C.

Bräse, S.

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Miniaturized microreactors enable photochemistry with laser irradiation in flow mode to convert azidobiphenyl into carbazole with
					high efficiency

Bremus-Köbberling, Elke

KITopen

1213Photochemistry with laser radiation in condensedphase using miniaturized photoreactorsElke Bremus-Köbberling1, Arnold Gillner1, Frank Avemaria2, Céline Réthoré2and Stefan Bräse*2,3Full Research Paper Open AccessAddress:1Fraunhofer Institute for Laser Technology, Steinbachstrasse 15,D-52074 Aachen, Germany, 2Institute of Organic Chemistry,Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, D-76131Karlsruhe, Germany and 3Institute of Toxicology and Genetics,Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1,D-76344 Eggenstein-Leopoldshafen, GermanyEmail:Stefan Bräse* - braese@kit.edu* Corresponding authorKeywords:azides; chemical diversity; flow chemistry; heterocycles; laser; microreactorBeilstein J. Org. Chem. 2012, 8, 1213–1218.doi:10.3762/bjoc.8.135Received: 31 March 2012Accepted: 18 June 2012Published: 31 July 2012This article is part of the Thematic Series "Recent developments inchemical diversity".Guest Editor: J. A. Porco Jr.© 2012 Bremus-Köbberling et al; licensee Beilstein-Institut.License and terms: see end of document.AbstractMiniaturized microreactors enable photochemistry with laser irradiation in flow mode to convert azidobiphenyl into carbazole withhigh efficiency.IntroductionClassical combinatorial chemistry [1,2] approaches usually aimat the synthesis of multi-milligram amounts of new compoundsto extend screening decks used in multiple screening campaigns[3]. An alternative method enabled by the maturing microreac-tion technology and the use of flow chemistry [4-6] is the inte-gration of synthesis and screening in one integrated lab-on-a-chip approach [7].Using this methodology we have integrated photochemistry in aminiaturized reaction setup to enable combinatorial flow chem-istry in lab-on-a-chip applications.Photochemical processes are in this case particularly interestingbecause of their enhanced molecular activation [8]. Photochem-istry in microreactors is an emerging research area [9], andespecially photocatalytic reactions have been investigated indetail by Matsushita et al. [10,11]. To date there are a couple ofreported examples combining miniaturized reaction systemswith synthetic laser photochemistry [5,6,9,12-28].The influence of photons, which are delivered via a suitablelight-transparent window, on the processes running in miniatur-ized photoreactors, is investigated with a focus on increasingBeilstein J. Org. Chem. 2012, 8, 1213–1218.1214Scheme 1: Synthesis of carbazole (2) by photolysis.the yield and selectivity as well as decreasing the reaction time.Photochemistry with laser radiation is a promising tool tobroaden the application spectrum of miniaturized systems, byfacilitating a powerful activation step due to a wide range ofavailable wavelengths and energy ranges [29,30]. Moreover, theoptical systems can be designed in a way that the reaction initia-tion by photons and an additional online analysis of the runningreaction is feasible.Results and DiscussionDesign and fabricationIn order to realize photochemical synthesis, several reactors andsmall reactor arrays with reaction volumes of approximately1 mL down to 35 µL were developed. These reactors were espe-cially designed for the stimulation of photochemical reactions(UV–vis radiation) as well as for demanding reaction condi-tions, such as the rapid elevation of temperature (with pulsedIR-laser radiation) or pressure pulses (due to the evaporation ofthe solvent upon the introduction of energy).Several microstructured reactor types were designed andproduced for reactions in the liquid phase. They are equippedwith quartz-glass cover plates, transparent to the laser radiation,pressed onto an appropriate sealing material. Moreover, chan-nels suitable for the mixing and reaction of two or moreisopycnic solutions were built in a polymer bloc by mechanicaltreatment [31]. The provision of bubble-free fluid is ensured inthis case by microchannels in at least two levels, which are builtfrom corresponding structured layers. These reactors were madeof polyether ether ketone (PEEK) and polytetrafluoroethylene(PTFE) [32] to study the influence of side reactions with thereactor material, which could reduce the yield of the desiredreaction product. The multilayer system is placed in a stainless-steel frame.With this type of reactor, it is possible to realize a series of reac-tions in parallel by arranging the reactor chambers in an (n × m)matrix. The microreactors applied for this study have four reac-tion chambers with varying volumes of the chambers due toincreasing depth, and different connections for the reagententrance (Figure 1).Figure 1: Four-fold PEEK-reactors with increasing chamber depthsfrom left to right and different techniques of fluid connection; top: gluedPEEK-capillaries, bottom: ¼ in. screw connections.PhotochemistryThe combinatorial synthesis of heterocycles and among them ofcarbazole is of particular interest since they are potential activepharmaceutical compounds [33-35]. The photolysis of 2-azido-biphenyl (1) with the help of a conventional UV-lamp has beenused for the synthesis of carbazole (2) since 1960 (Scheme 1)[36-39].Beilstein J. Org. Chem. 2012, 8, 1213–1218.1215However, there are only a few examples of substituted productsobtained by this reaction, and several side-products, such as thecorresponding azo-derivatives, are usually formed [36,40-44].During the past few years, we successfully employed triazeneresins, such as 4, which are readily available from aniline in thesynthesis of a library of aromatic derivatives [45-48]. Moreover,triazene-resins are perfectly suitable for the synthesis ofarylazides 5 (Scheme 2) [49].Scheme 2: Synthesis of arylazides 2 by solid-phase synthesis.The photochemical decomposition of arylazides into carbazolesis appropriate for application in miniaturized photoreactors,since significant results can be observed by an online analysisthrough HPLC and GC [50]. Because of the miniaturization,online analysis is especially suitable for our setup.We therefore investigated whether the photoreaction can berealized in miniaturized photoreactors and to what extent theuse of a laser as a photon source is advantageous. The irradi-ation of 2-azidobiphenyl (1) in methanol with a conventionalxenon lamp (400 W, λ > 345 nm) required 18 h for 50% yield(95% selectivity) in a 10 mm cell with an 8 mm light-exposurediameter (Figure 2).Figure 2: Photolysis results in batch setup (flask) with a xenon lamp(400 W, λ > 345 nm).Figure 3: Carbazole synthesis in miniaturized photoreactors Type II(PEEK and Teflon), flow control, P = 0.92 W.Figure 4: Carbazole synthesis in miniaturized photoreactors Type II(PEEK and Teflon), power control, flow 26 mL/h.Frequency-tripled Nd:YAG laser radiation (λ = 355 nm, 8 kHzpulse frequency; pulse duration 26 ns) was chosen because thewavelength is close to that of the applied UV-lamp, 355 nm isusually within the absorption area of azides, and this laser typeis commonly used in most laser labs. We applied a single-pulsepower of 0.16 to 3 W resulting in pulse energies between 4and 87 nJ and energy densities of approximately 0.02 to0.17 µJ/cm2 within a defocused laser spot of 0.2 to 0.5 cm2, tocarry out the same reaction (Scheme 1), but carbazole wasobtained much faster from 2-azidobiphenyl (1). Compared toconventional UV sources, the use of laser irradiation clearlyaccelerated the reaction: from 18 h (Xe lamp, Figure 2) to 30 s(Nd:YAG laser) for 50% yield and 95% selectivity, calculatedfrom the data presented in Figure 3. This reaction was success-fully carried out in a miniaturized photoreactor (Figures 3–6).The monomolecular reaction can be realized by using laser radi-ation of 355 nm wavelength as a photon source, in a clean way,avoiding almost completely the formation of the undesiredBeilstein J. Org. Chem. 2012, 8, 1213–1218.1216Figure 5: Test setup with continuously operating, miniaturizedphotoreactor.Figure 6: The miniaturized photoreactor (PEEK) during photolysis.diazo derivatives 3. The side reaction is supposedly reduced dueto a lesser effect of heating owing to the small bandwidth irradi-ation and minimized exposure time through the miniaturizedflow setup.During these tests, it was shown that a largely better selectivitycan be achieved, compared to the one obtained in a standard UVirradiation setup (Figure 2). Experiments were performed inbatch as well as flow-injection configuration. The continuousprocess used allowed us to vary the residence time in the reactorby regulating the flow speed of the reactant solution, with thehelp of a syringe pump (Figure 5).For this study, reactors made of PEEK, as well as PTFE reac-tors were used, leading to similar yields of carbazole (Figure 3and Figure 4), showing no major influence of the reactor ma-terial on the reaction.The deviations from linearity in the low power area of Figure 4can be attributed to fluctuations of the laser power. For thehigh-power area, a correlation between yield, power and reac-tion time, which can be explained by kinetics, is observed.ConclusionThe preparation and application of polymeric, miniaturizedphotoreactors, equipped for the effective use of photons in thereaction chamber, provided by frequency-converted lasersources, was successfully shown.With these reactors or reactor components, the photonic influ-ence on reactions in miniaturized photoreactors was proven tobe useful in parameter studies in which laser power and flowrate were varied.The advantages of laser chemistry in the condensed phasecompared to standard photochemical approaches have beenshown in this preliminary study, proving the suitability of laserphotochemistry for organic synthesis. Thanks to the furtherminiaturization and the availability of new moderately pricedlaser systems even better suited beam sources can be providedfor photochemistry.In the described experiments, laser radiation of 355 nm wave-length (frequency-tripled Nd:YAG) was used. Since the spec-tral range of interest for most photoreactions ranges from theultraviolet to the visible region, tunable laser systems (opticalparametric oscillators) feature promising properties for usephotochemical experiments. Thus, the irradiation wavelengthcan be adapted to the needs of the reaction (e.g., to a shiftedabsorption maximum of the reactant due to substitution) facili-tating a large range of applications of this technique. Further-more, IR laser sources (diode laser, Nd:YAG laser, CO2 laser)could be applied for pulsed temperature and pressure elevationin microreactors, as well as microwave stimulation to accel-erate reactions.ExperimentalAll starting materials and products were characterized by stan-dard techniques (1H NMR, 13C NMR, and elemental analysis)and are compared with authentic samples. The products wereanalyzed by GC–MS (internal standard, dodecane) and/orHPLC.A solution of 2-azidobiphenyl (1) was continuously added to aminiaturized reactor of type II (see Figure 1, dimension of thereactor chamber 3 × 5 mm, 35 μL volume) with a syringe pump.The chamber was continuously irradiated with a Nd:YAG laser(355 nm). At a constant flow of 26 mL/h, the laser-pulse powerwas varied from 0.16 to 1.28 W. Furthermore, at a constantBeilstein J. Org. Chem. 2012, 8, 1213–1218.1217intermediate power of 0.92 W the flow rate (10 to 100 mL/h)and therefore the dwell time (exposure time) in the reactor wasvaried. The yield was determined by HPLC.Supporting InformationSupporting Information File 1Description of the flow reactor setup, kinetics, experimentalprocedures and spectroscopic data of all compounds.[http://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-8-135-S1.pdf]AcknowledgementsWe thank the Fonds der Chemischen Industrie for financialsupport.References1. Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds. Handbook ofCombinatorial Chemistry; VCH: Weinheim, Germany, 2002.2. Ehrfeld, W.; Hessel, V.; Löwe, H. Microreactors – New Technology forModern Chemistry; Wiley-VCH: Weinheim, Germany, 2000.3. Chen, I.-J.; Hubbard, R. E. J. Comput.-Aided Mol. Des. 2009, 23,603–620. doi:10.1007/s10822-009-9280-54. Ley, S. V.; Baxendale, I. R. Chimia 2008, 62, 162–168.doi:10.2533/chimia.2008.1625. Wirth, T., Ed. Microreactors in Organic Synthesis and Catalysis;Wiley-VCH: Weinheim, Germany, 2008.6. Yoshida, J.-i., Ed. Flash Chemistry: Fast Organic Synthesis inMicrosystems; John Wiley & Sons: Chichester, U.K., 2008.7. Bapna, A.; Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.;Fan, T.-P. D.; Ley, S. V. Org. Biomol. Chem. 2004, 2, 611–620.doi:10.1039/b313414h8. McNaught, A. D.; Wilkinson, A. IUPAC. Compendium of ChemicalTerminology, 2nd ed.; Blackwell Scientific Publications: Oxford, U.K.,1997.9. Coyle, E. E.; Oelgemöller, M. Photochem. Photobiol. Sci. 2008, 7,1313–1322. doi:10.1039/b808778d10. Matsushita, Y.; Iwasawa, M.; Suzuki, T.; Ichimura, T. Chem. Lett. 2009,38, 846–847. doi:10.1246/cl.2009.84611. Matsushita, Y.; Ohba, N.; Suzuki, T.; Ichimura, T. Catal. Today 2008,132, 153–158. doi:10.1016/j.cattod.2007.12.07812. The preliminary work has been submitted as patent: Bremus, E.;Gillner, A.; Bräse, S.; Köbberling, J. PCT Int. Appl. (2000), WO2000062929 A2 20001026. Language: German, Database: CAPLUSand described in [36]. The reactor and the photochemistry of azideshave also been the subject of various public presentations since 2002without the details being disclosed.13. Kirschning, A. Beilstein J. Org. Chem. 2011, 7, 1046–1047.doi:10.3762/bjoc.7.119See also the Thematic Series “Chemistry in flow systems II”.14. Oelgemöller, M.; Shvydkiv, O. Molecules 2011, 16, 7522–7550.doi:10.3390/molecules16097522See for a recent review.15. Davis, R. H.; Palmer, D. D. Apparatus and method for performingphotochemical reactions. WO Patent WO2005123241 , Dec 29, 2005.16. For a commercial photo-microreactor see:http://www.ymc-europe.com/ymceurope/products/flow-chemistry/flow-chemistry-start.html#keychemlumino17. Nindl, G.; Hess, W.; Waite, L. R.; Balcavage, W. X.Biomed. Sci. Instrum. 2005, 41, 187–192.18. Peterson, D. S.; Rohr, T.; Svec, F.; Fréchet, J. M. J. Anal. Chem. 2003,75, 5328–5335. doi:10.1021/ac034108j19. Ouchi, A.; Sakai, H.; Oishi, T.; Kaneda, M.; Suzuki, T.; Saruwatari, A.;Obata, T. J. Photochem. Photobiol., A 2008, 199, 261–266.doi:10.1016/j.jphotochem.2008.05.02420. Bourne, R. A.; Han, X.; Poliakoff, M.; George, M. W.Angew. Chem., Int. Ed. 2009, 48, 5322–5325.doi:10.1002/anie.20090173121. Lu, H.; Schmidt, M. A.; Jensen, K. F. Lab Chip 2001, 1, 22–28.doi:10.1039/b104037p22. Goodell, J. R.; McMullen, J. P.; Zaborenko, N.; Maloney, J. R.;Ho, C.-X.; Jensen, K. F.; Porco, J. A., Jr.; Beeler, A. B. J. Org. Chem.2009, 74, 6169–6180. doi:10.1021/jo901073v23. Pimparkar, K.; Yen, B.; Goodell, J. R.; Martin, V. I.; Lee, W.-H.;Porco, J. A., Jr.; Beeler, A. B.; Jensen, K. F. J. Flow Chem. 2011, 1,53–55. doi:10.1556/jfchem.2011.0000624. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J.Angew. Chem., Int. Ed. 2012, 51, 4144–4147.doi:10.1002/anie.20120096125. Vasudevan, A.; Villamil, C.; Trumbull, J.; Olson, J.; Sutherland, D.;Pan, J.; Djuric, S. Tetrahedron Lett. 2010, 51, 4007–4009.doi:10.1016/j.tetlet.2010.05.11926. Fuse, S.; Tanabe, N.; Yoshida, M.; Yoshida, H.; Doi, T.; Takahashi, T.Chem. Commun. 2010, 46, 8722–8724. doi:10.1039/c0cc02239j27. Mimieux Vaske, Y. S.; Mahoney, M. E.; Konopelski, J. P.;Rogow, D. L.; McDonald, W. J. J. Am. Chem. Soc. 2010, 132,11379–11385. doi:10.1021/ja105002328. Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47,4583–4592. doi:10.1039/c0cc05060a29. Davies, D. M. E.; Murray, C.; Berry, M.; Orr-Ewing, A. J.;Booker-Milburn, K. I. J. Org. Chem. 2007, 72, 1449–1457.doi:10.1021/jo062316g30. Hara, M.; Tojo, S.; Majima, T. J. Phys. Chem. A 2003, 107,4778–4783. doi:10.1021/jp027002l31. Nagy, K. D.; Shen, B.; Jamison, T. F.; Jensen, K. F.Org. Process Res. Dev. 2012, 16, 976–981. doi:10.1021/op200349f32. Peterson, T. P.; Polyzos, A.; O’Brien, M.; Ulven, T.; Baxendale, I. R.;Ley, S. V. ChemSusChem 2012, 5, 274–277.33. Bräse, S.; Banert, K. Organic Azides – Syntheses and Applications;Wiley: Chichester, U.K., 2009.See for the use of azides in heterocycle chemistry.34. Stokes, B. J.; Jovanović, B.; Dong, H.; Richert, K. J.; Riell, R. D.;Driver, T. G. J. Org. Chem. 2009, 74, 3225–3228.doi:10.1021/jo9002536And references cited therein.35. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.;Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184–16186.doi:10.1021/ja806543s36. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. 2005,117, 5320–5374. doi:10.1002/ange.200400657Angew. Chem., Int. Ed. 2005, 44, 5188–5240.doi:10.1002/anie.200400657 See for reactions and safety issues ofazides.37. Swenton, J. S.; Ikeler, T. J.; Williams, B. H. J. Am. Chem. Soc. 1970,92, 3103–3109. doi:10.1021/ja00713a031Beilstein J. Org. Chem. 2012, 8, 1213–1218.121838. Sundberg, R. J.; Heintzelman, R. W. J. Org. Chem. 1974, 39,2546–2552. doi:10.1021/jo00931a02039. Sundberg, R. J.; Gillespie, D. W.; DeGraff, B. A. J. Am. Chem. Soc.1975, 97, 6193–6196. doi:10.1021/ja00854a04240. Platz, M. S. Acc. Chem. Res. 1995, 28, 487–492.doi:10.1021/ar00060a00441. Meth-Cohn, O. Heterocycles 1980, 14, 1497–1516.doi:10.3987/R-1980-10-149742. Hawkins, D. G.; Meth-Cohn, O. J. Chem. Res., Miniprint 1982,1218–1225.43. Albini, A.; Bettinetti, G.; Minoli, G. J. Chem. Soc., Perkin Trans. 2 1999,2803–2807. doi:10.1039/a903863i44. Forbes, E. J.; Tatlow, J. C.; Wragg, R. T. Tetrahedron 1960, 8, 73–78.45. Bräse, S. Acc. Chem. Res. 2004, 37, 805–816. doi:10.1021/ar020014546. Bräse, S.; Enders, D.; Köbberling, J.; Avemaria, F. Angew. Chem.1998, 110, 3614–3616.doi:10.1002/(SICI)1521-3757(19981217)110:24<3614::AID-ANGE3614>3.0.CO;2-RAngew. Chem., Int. Ed. 1998, 37, 3413–3415.doi:10.1002/(SICI)1521-3773(19981231)37:24<3413::AID-ANIE3413>3.0.CO;2-K47. Bräse, S.; Schroen, M. Angew. Chem. 1999, 111, 1139–1142.doi:10.1002/(SICI)1521-3757(19990419)111:8<1139::AID-ANGE1139>3.0.CO;2-FAngew. Chem., Int. Ed. 1999, 38, 1071–1073.doi:10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO;2-948. Hafner, A.; Bräse, S. Angew. Chem. 2012, 124, 3773–3775.doi:10.1002/ange.20110741449. Avemaria, F.; Zimmermann, V.; Bräse, S. Synlett 2004, 1163–1166.doi:10.1055/s-2004-8229850. Bou-Hamdan, F. R.; Lévesque, F.; O'Brien, A. G.; Seeberger, P. H.Beilstein J. Org. Chem. 2011, 7, 1124–1129. doi:10.3762/bjoc.7.129See for a related work leading to azepinones.License and TermsThis is an Open Access article under the terms of theCreative Commons Attribution License(http://creativecommons.org/licenses/by/2.0), whichpermits unrestricted use, distribution, and reproduction inany medium, provided the original work is properly cited.The license is subject to the Beilstein Journal of OrganicChemistry terms and conditions:(http://www.beilstein-journals.org/bjoc)The definitive version of this article is the electronic onewhich can be found at:doi:10.3762/bjoc.8.135

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