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2004 | 2 | 2 | 302-322
Tytuł artykułu

RuO4-mediated oxidation ofN-benzylated tertiary amines. Are amineN-oxides and iminium cations reaction intermediates?

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
N-Benzylmorpholine,-piperidine, and-pyrrolidine (1A-C, resp.) are oxidised by RuO4 (generatedin situ) at both endocyclic and exocyclic (benzylic)N-α-methylene positions to afford lactams (and dioxo-derivatives) and benzaldehyde (and benzoyl derivatives), respectively. TheN-oxides of1A-C, formed by a minor side reaction, are not involved as intermediates. Control experiments showed the transient formation of endo- and exocyclic iminium cations trapped with NaCN as the corresponding nitriles. The proposed course of the RuO4-mediated oxidation of1A-C involves the consecutive steps1⇒iminium cations+cyclic enamine⇒oxidation products. The endocyclic/exocyclic regioselectivity of the oxidation reaction lies between 0.8 (for1A) and 2.1 (for1B). The amine cation radical and theN-α-C· carbon-centered radical seem not to be involved.
Wydawca

Czasopismo
Rocznik
Tom
2
Numer
2
Strony
302-322
Opis fizyczny
Daty
wydano
2004-06-01
online
2004-06-01
Twórcy
  • Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania, hpetride@cco.ro
  • Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania
  • Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania
  • Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania
Bibliografia
  • [1] C. Djerassi and R.R. Engle: “Oxidations with Ruthenium Tetroxide”,J. Am. Chem. Soc., Vol. 75, (1953), pp. 3838–3840. http://dx.doi.org/10.1021/ja01111a507[Crossref]
  • [2] E.S. Gore: “Ruthenium-catalyzed Oxidations of Organic Compounds”,Platinum Met. Rev., Vol. 27, (1983), pp. 111–125.
  • [3] J.L. Courtney: “Ruthenium tetroxide oxidations,” In: W.J. Mijs and C.R.H.I. De Jonge (Eds.):Org. Synth. Oxid. Met. Compd., Plenum Press, New York, 1986, pp. 445–467.
  • [4] L.M. Berkowitz and P.N. Rylander: “Use of Ruthenium Tetroxide as a Multi-purpose Oxidant”,J. Am. Chem. Soc., Vol. 80, (1958), pp. 6682–6684. http://dx.doi.org/10.1021/ja01557a053[Crossref]
  • [5] P.H.J. Carlsen, T. Katsuki, V.S. Martin and K.B. Sharpless: “A Greatly Improved Procedure for Ruthernium Tetraoxide Catalyzed Oxidations of Organic Compounds,”J. Org. Chem., Vol. 46, (1981), pp. 3936–3938. http://dx.doi.org/10.1021/jo00332a045[Crossref]
  • [6] M.T. Nuñez and V.S. Martin: “Efficient Oxidation of Phenyl Groups to Carboxylic Acids with Ruthenium Tetraoxide. A Simple Synthesis of (R)-γ-Caprolactone, the Pheromone ofTrogoderma granarium”,J. Org. Chem., Vol. 55, (1990), pp. 1928–1932. http://dx.doi.org/10.1021/jo00293a044[Crossref]
  • [7] W.P. Griffith, A.G. Shoair and M. Suriaatmaja: “Ruthenium-catalysed cleavage of alkenes and alkynes to carboxylic acids”,Synth. Commun., Vol. 30, (2000), pp. 3091–3096. http://dx.doi.org/10.1080/00397910008086915[Crossref]
  • [8] L. Albarella, D. Musumeci and D. Sica: “Reactions of 1,5-Dienes with Ruthenium Tetraoxide: Stereoselective Synthesis of Tetrahydrofurandiols”,Eur. J. Org. Chem., (2001), pp. 997–1004. [Crossref]
  • [9] S. Torii, T. Inokuchi and K. Kondo: “A Facile Procedure for Oxidative Cleavage of Enolic Olefins to the Carbonyl Compounds with Ruthenium Tetraoxide (RuO4)”,J. Org. Chem., Vol. 50, (1985), pp. 4980–4982. http://dx.doi.org/10.1021/jo00224a071[Crossref]
  • [10] M.-P. Denieul, B. Laursen, R. Hazell and T. Skrydstrup: “Synthesis of the Benzophenone Fragment of Balanol via an Intramolecular Cyclization Event”,J. Org. Chem., Vol. 65, (2000), pp. 6052–6060. http://dx.doi.org/10.1021/jo000750r[Crossref]
  • [11] H. Tanaka: “Oxidation Reaction of Steroid Alcohols by Ruthenium Tetroxide”,Tetrahedron, Vol. 19, (1969), pp. 1959–1963.
  • [12] F.X. Webster, J. Rivas-Enterrias and R.M. Silvestein: “Synthesis of Diacids and Keto Acids by Ruthenium Tetraoxide Catalyzed Oxidation of Cyclic Allylic Alcohols and α,β-Unsaturated Ketones”,J. Org. Chem., Vol. 52, (1987), pp. 689–691. http://dx.doi.org/10.1021/jo00380a040[Crossref]
  • [13] P.E. Morris Jr and D.E. Kielly: “Ruthenium Tetraoxide Phase-Transfer-Promoted Oxidation of Secondary Alcohols to Ketones”,J. Org. Chem., Vol. 52, (1987), pp. 1149–1152. http://dx.doi.org/10.1021/jo00382a035[Crossref]
  • [14] S. Giddings and A. Mills: “Optimization of a Simple System for the Oxidation of Octan-2-ol with Sodium Bromate, Mediated by Ruthenium Tetraoxide Generatedin situ”,J. Org. Chem., Vol. 53, (1988), pp. 1103–1107. http://dx.doi.org/10.1021/jo00240a037[Crossref]
  • [15] J.A. Caputo and R. Fuchs: “The Oxidations of Cyclobutanols and Aromatic Rings with Ruthenium Tetroxide”,Tetrahedron Lett., (1967), pp. 4729–4731. [Crossref]
  • [16] K.C. Ramey, D.C. Lini, R.M. Moriarty, H. Gopal and H.G. Welsh: “Analysis of the Nuclear Magnetic Resonance Spectra of Some 2,6-Bridged Bicyclo[2.2.1]heptane Derivatives”,J. Am. Chem. Soc., Vol. 89, (1967), pp. 2401–2408. http://dx.doi.org/10.1021/ja00986a028[Crossref]
  • [17] A. Mills and C. Holland: “Effect of Ultrasound on the Kinetics of Oxidation of Octan-2-ol and Other Secondary Alcohols with Sodium Bromate, Mediated by Ruthenium Tetraoxide in a Biphasic System”,Ultrason. Sonochem., Vol. 2, (1995), pp. 533–538.
  • [18] S. Rajendran and D.C. Trivedi: “Ruthenium Tetroxide as a Phase Transfer Catalyst in Biphasic System and Its in situ Electrochemical Regeneration: Oxidation of Aromatic Primary Alcohol and Aldehydes”,Synthesis, (1995), pp. 153–154.
  • [19] A.K. Chakraborti and U.R. Ghatak: “Extension of an Improved Procedure for the Ruthenium Tetraoxide-Catalyzed Degradation of Aromatic Rings: A Highly Efficient and Stereocontrolled Synthesis of Functionalized Bridged-Ring and Carbocyclic Esters”,Synthesis, (1983), pp. 746–748.
  • [20] V.S. Martin, m.T. Nuñez and C.E. Tonn: “Easy and General Method to Synthesize Chiral 2-Hydroxyacid Benzoates”,Tetrahedron Lett., Vol. 29, (1988), pp. 2701–2702. http://dx.doi.org/10.1016/0040-4039(88)85264-X[Crossref]
  • [21] S. Torii, T. Inokuchi, S. Matsumoto, T. Saeki and T. Oki: “Indirect Electrooxidation by using Ruthenium Tetraoxide and Chloride Ion as Recycling Mediators. Optimization for the Oxidation of Diisopropylidene-D-glucose to the Ulose”,Bull. Chem. Soc. Jpn., Vol. 62, (1989), pp. 2108–2110. http://dx.doi.org/10.1246/bcsj.62.2108[Crossref]
  • [22] A. Naundorf, S. Natsch and W. Klaffe: “A convenient route to keto-glycosyl phosphates”,Tetrahedron Lett., Vol. 41, (2000), pp. 189–192. http://dx.doi.org/10.1016/S0040-4039(99)02020-1[Crossref]
  • [23] M. Panda and S.C. Pati: “Ruthenium (VIII) mediated oxidation of some aliphatic and alicyclic ketones by periodate-ruthenium (III) system in aqueous HClO4 medium”,Int. J. Chem. Kinet., Vol. 28, (1996), pp. 453–460. http://dx.doi.org/10.1002/(SICI)1097-4601(1996)28:6<453::AID-KIN7>3.0.CO;2-U[Crossref]
  • [24] J.M. Bakke and A.E. Frøhaug: “The Mechanism of RuO4-Mediated Oxidations of Ethers: Isotope Effects, Solvent Effects and Substituent Effects”,Acta Chem. Scand., Vol. 49, (1995), pp. 615–622. http://dx.doi.org/10.3891/acta.chem.scand.49-0615[Crossref]
  • [25] P.F. Schuda, M.B. Cichowicz and M.R. Heimann: “A Facile Method for the Oxidation Removal of Benzyl Ethers: the Oxidation of Benzyl Ethers to Benzoates by Ruthenium Tetraoxide”,Tetrahedron Lett., Vol. 24, (1983), pp. 3829–3830. http://dx.doi.org/10.1016/S0040-4039(00)94286-2[Crossref]
  • [26] R.S. Glass and J.L. Broeker: “Synthesis, Crystal, and Molecular Structures and Conformations of Naphto[1,8-b,c]-1,5-dithiocin-1,1-dioxide,-1,5-dioxide,-1,1,5-trioxide and-1,1,5,5-tetraoxide”,Tetrahedron, Vol. 47, (1991), pp. 5077–5086. http://dx.doi.org/10.1016/S0040-4020(01)87120-9[Crossref]
  • [27] J.M. Bakke and A.E. Frøhaug: “Ruthenium Tetraoxide Mediated Reactions: the Mechanisms of Oxidations of Hydrocarbons and Ethers”,J. Phys. Org. Chem., Vol. 9, (1996), pp. 310–318 and references therein. http://dx.doi.org/10.1002/(SICI)1099-1395(199606)9:6<310::AID-POC790>3.0.CO;2-E[Crossref]
  • [28] D.G. Lee and M. van den Engh: “The Oxidation of Tetrahydrofuran by Ruthenium Tetroxide”,Can. J. Chem., Vol. 50, (1972), pp. 3129–3134. http://dx.doi.org/10.1139/v72-501[Crossref]
  • [29] G. Bettoni, C. Franchini, F. Morlacchi, N. Tangari and V. Tortorella: “Reactions of Nitrogen Compounds with Ruthenium Tetroxide. 2. Oxidation of Tertiary Amines as a Convenient Alternative to von Braun Degradation”,J. Org. Chem., Vol. 41, (1976), pp. 2780–2782. http://dx.doi.org/10.1021/jo00878a034[Crossref]
  • [30] R. Perrone, G. Bettoni and V. Tortorella: “Oxidation of Morpholine Derivatives with Ruthenium (VIII) Oxide”,Synthesis, (1976), pp. 598–600.
  • [31] N. Tangari, M. Giovine, F. Morlacchi and C. Vetuschi: “Oxidation of Organic Nitrogen Compounds by means of Ruthenium Tetroxide: Selective Preparation ofN-Substituted Lactams”,Gazz. Chim. Ital., Vol. 115, (1985), pp. 325–328.
  • [32] J.C. Sheehan and R.W. Tulis: “Oxidation of Cyclic Amines with Ruthenium Tetroxide”,J. Org. Chem., Vol. 39, (1974), pp. 2264–2267. http://dx.doi.org/10.1021/jo00929a030[Crossref]
  • [33] G. Bettoni, G. Carbonara, C. Franchini and V. Tortorella: “Oxidation of Tertiary Polycyclic Amines by RuO4”,Tetrahedron, Vol. 31, (1981), pp. 4159–4164. http://dx.doi.org/10.1016/0040-4020(81)85006-5[Crossref]
  • [34] C. Vetuschi, N. Tangari, M. Giovine, C. Franchini and V. Tortorella: “Selective Oxidation of Piperazine Derivatives with Ruthenium Tetroxide”,Farmaco, Vol. 47, (1992), pp. 599–605.
  • [35] S. Yoshifuji, Y. Arakawa and Y. Nitta: “Ruthenium Tetroxide Oxidation of 1-Azabicycloalkan-2-ones”,Chem. Pharm. Bull., Vol. 33, (1985), pp. 5042–5047. [Crossref]
  • [36] S. Yoshifuji, Y. Arakawa and Y. Nitta: “Ruthenium Tetroxide Oxidation ofN-Alkyllactams”,Chem. Pharm. Bull., Vol. 36, (1987), pp. 357–363. [Crossref]
  • [37] K. Tanaka, S. Yoshifuji and Y. Nitta: “A New Method for the Synthesis of Amides from Amines: Ruthenium Tetroxide Oxidation ofN-Protected Alkylamines”,Chem. Pharm. Bull., Vol. 36, (1988), pp. 3125–3129. [Crossref]
  • [38] L.N. Mander and C.M. Williams: “Oxidative degradation of benzene rings”,Tetrahedron, Vol. 59, (2003), pp. 1105–1136. http://dx.doi.org/10.1016/S0040-4020(02)01492-8[Crossref]
  • [39] W. Tochtermann, M. Haase and R. Dibben: “Makrocyclishe Bis-α-Diketone”,Tetrahedron Lett., Vol. 29, (1988), pp. 189–190. http://dx.doi.org/10.1016/S0040-4039(00)80049-0[Crossref]
  • [40] S. Tanji, Y. Kodaka, T. Shibata and K. Soai: “Synthesis of Chiral α-Acetoxy-N-acetylamides from Chiral Pyrimidylalkanols by the Oxidative Cleavage of Pyrimidine Ring”,Heterocycles, Vol. 52, (2000), pp. 151–158. http://dx.doi.org/10.3987/COM-98-S1[Crossref]
  • [41] J.M. Bakke and D. Bethell: “The Mechanism of RuO4-Mediated Oxidations of Saturated Hydrocarbons. Reactivity, Kinetic Isotope Effect and Activation Parameters”,Acta Chem. Scand., Vol. 46, (1992), pp. 644–649. http://dx.doi.org/10.3891/acta.chem.scand.46-0644[Crossref]
  • [42] J.M. Bakke, A.E. Frøhaug: “The Mechanism of RuO4-Mediated Oxidations of Saturated Hydrocarbons. Solvent Effects and Substituent Effects”,Acta Chem. Scand., Vol. 48, (1994), pp. 160–164. http://dx.doi.org/10.3891/acta.chem.scand.48-0160[Crossref]
  • [43] J.L. Coudret, S. Zöllner, B.J. Ravoo, L. Malara, C. Hanisch, K. Dörre, A. de Meijere and B. Waegell: “Role of Cyclopropanes as Activating Groups During Oxidation Reactions with RuO4 Generatedin situ”,Tetrahedron Lett., Vol. 37, (1996), pp. 2425–2428 and references therein. http://dx.doi.org/10.1016/0040-4039(96)00325-5[Crossref]
  • [44] A Mills and C. Holland: “Investigation into the Nature of the Oxoruthenate Species used to Mediate the Oxidation of an Organic Substrate by Hypochlorite in Biphasic System”,J. Chem. Res. Synop., (1997), pp. 368–369. [Crossref]
  • [45] G. Green, W.P. Griffith, D.M. Hollinshead, S.V. Ley and M. Schröder: “Oxo complexes of Ruthenium (VI) and (VII) as Organic Oxidants”,J. Chem. Soc. Perkin Trans. 1, (1984), pp. 681–686. [Crossref]
  • [46] M. Bietti, A. Cuppoletti, C. Dagostin, C. Florea, C. Galli, P. Gentili, H. Petride and C. Russo Caia: “Stereoelectronic Inhibition of Deprotonation in the Radical Cation ofN-Benzylpiperidine: a Contribution to the Debate on the Mechanism ofN-Dealkylation of Tertiary Amines”,Eur. J. Org. Chem., (1998), pp. 2425–2429. [Crossref]
  • [47] A. Cuppoletti, C. Dagostin, C. Florea, C. Galli, P. Gentili, O. Lanzalunga, A. Petride and H. Petride: “The Iron Porphyrin Induced Oxidation ofN-Benzyl Aziridine: Radicalvs. Electron Transfer Mechanism”,Chem. Eur. J., Vol. 5, (1999), pp. 2993–2999. http://dx.doi.org/10.1002/(SICI)1521-3765(19991001)5:10<2993::AID-CHEM2993>3.0.CO;2-C[Crossref]
  • [48] M. Cãproiu, C. Florea, C. Galli, A. Petride and H. Petride: “Oxidation ofN-Benzyl Aziridine by Molecular Iodine: Competition of Electron Transfer and Heterolytic Pathways”,Eur. J. Org. Chem., (2000), pp. 1037–1043. [Crossref]
  • [49] C. Drãghici, C. Florea, C. Galli, A. Petride and H. Petride: “Electron Transfervs. Heterolytic Reactions. Behaviour ofN-Benzyl Aziridine Towards (aqua)xCuII and batho2CuII Ions”,ARKIVOC, (2002), pp. 109–122 (http://www.arkatusa.org/ark/journal/2002/Nenitzescu/CN-196A/196A.pdf).
  • [50] A. Cuppoletti, C. Galli, P. Gentili and H. Petride: “A Radical Route in the Biomimetic Oxidation of a Tertiary Amine”,J. Phys. Org. Chem., Vol. 15, (2002), pp. 672–675. http://dx.doi.org/10.1002/poc.533[Crossref]
  • [51] H. Petride et al., in preparation.
  • [52] The partial NMR data (ppm) ofunk are: δH = 2.97 (2H, t,J=5.6 Hz, C(x)H 2) coupled with 3.10 (2H, t,J=5.6 Hz, C(y)H 2), 4.46 (2H, s, benzyl); δC = 44.7 (C(x)), 47.1 (C(y) or benzyl), 47.2 (benzyl orC(y)), 169.8 (N-CO?). TheCO signal is longrange coupled with all citedH’s.
  • [53] From1C (ppm): δH = 6.83 (1H, t,H para ), 6.87 (2H, d,H ortho ), and 7.19 (2H, t,H meta ); δC = 115.6 (C ortho ), 119.4 (C para ), 129.4 (C meta ), and 158.4 (C ipso ). Similar data were obtained also from1A or1B.
  • [54] For a CCl4/water (1/1, v/v) mixture, 98% of RuO4 lies in the organic phase (see ref.|12a|). http://dx.doi.org/10.3891/acta.chem.scand.46-0644[Crossref]
  • [55] N.J. Leonard and F.P. Hauck Jr.: “Unsaturated Amines. X. The Mercuric Acetate Route to Substituted Piperidines, Δ2-Tetrahydropyridines and Δ2-Tetrahydroanabasines”,J. Am. Chem. Soc., Vol. 79, (1957), pp. 5279–5292. http://dx.doi.org/10.1021/ja01576a056[Crossref]
  • [56] D.S. Gierson, M. Harris and H.P. Husson: “Synthesis and Chemistry of 5,6-Dihydropyridinium Salt Adducts. Synthons for General Electrophilic and Nucleophilic Substitution of the Piperidine Ring System”,J. Am. Chem. Soc., Vol. 102, (1980), pp. 1064–1082. http://dx.doi.org/10.1021/ja00523a026[Crossref]
  • [57] B. Ho and N. Castagnoli, Jr.: “Trapping of metabolically generated electrophilic species with cyanide ion: metabolism of 1-benzylpyrrolidine”,J. Med. Chem., Vol. 23, (1980), pp. 133–139. http://dx.doi.org/10.1021/jm00176a006[Crossref]
  • [58] A. Koskinen and M. Lounasmaa: “Regiospecific Functionalisation of Carbon Atoms α to Heterocyclic Nitrogen”,Tetrahedron, Vol. 39, (1983), pp. 1627–1633. http://dx.doi.org/10.1016/S0040-4020(01)88573-2[Crossref]
  • [59] L.M. Sayre, D.A. Engelhart, B. Venkataraman, M.K.M. Babu and G.D. McCoy: “Generation and fate of enamines in the microsomal metabolism of cyclic tertiary amines”,Biochem. Biophys., Res. Commun., Vol. 179, (1991), pp. 1368–1376. http://dx.doi.org/10.1016/0006-291X(91)91724-Q[Crossref]
  • [60] A. Dornow and H. Thies: “Über die Umsetzung von Nitroessigsäureä thylester mit Mannich-Basen”,J. Liebigs Ann. Chem., Vol. 581, (1953), pp. 219–224. http://dx.doi.org/10.1002/jlac.19535810123[Crossref]
  • [61] M. Kerfanto, A. Brault, F. Venien, J.M. Morvan and A. Le Rouzic: “Gem-Di(N-amine) Compounds. I. Generalities. Effect of water”,Bull. Soc. Chim. France, (1975), pp. 196–200.
  • [62] E.F. Curragh, H.B. Henbest and A. Thomas: “Amine Oxidation. Part VII. Cleavage of Tetra-N-substituted 1,2-Diamines by Manganese Dioxide”,J. Chem. Soc., (1960), pp. 3559–3563. [Crossref]
  • [63] M. Schröder: “Osmium Tetraoxide. Cis Hydroxylation of Unsaturated Substrates”,Chem. Rev., Vol. 80, (1980), pp. 187–213. http://dx.doi.org/10.1021/cr60324a003[Crossref]
  • [64] J.P. Mason and M.J. Zief: “4-Morpholinomethyl Alkyl Ethers and N-Substituted Morpholines”,J. Am. Chem. Soc., Vol. 62, (1940), pp. 1450–1452. http://dx.doi.org/10.1021/ja01863a034[Crossref]
  • [65] T.J. King: “The Reduction of Allylamines with Sodium in Liquid Ammonia”,J. Chem. Soc., (1951), pp. 898–900. [Crossref]
  • [66] A.R. Surrey, S.O. Winthrop, M.K. Rukwid and B.F. Tullar: “The Preparation of N-Benzyl-3-morpholones and N-Benzyl-3-homomorpholones from N-(Hydroxyalkyl)-chloroacetamides”,J. Am. Chem. Soc., Vol. 77, (1955), pp. 633–636. http://dx.doi.org/10.1021/ja01608a031[Crossref]
  • [67] C. Kashima and K. Harada: “Synthesis and Reaction of Optically Active Morpholinones”,J. Chem. Soc. Perkin Trans. 1, (1988), pp. 1521–1526. [Crossref]
  • [68] B.M. Pinto, D.M. Vyas and W.A. Szarek: “Synthetic routes to nucleoside analogs ofN-substituted 1-oxa-4-azacyclohexanes and 1-thia-4-azacyclohexanes.13C Nuclear magnetic resonance spectra of six-membered, cyclic amides”,Can. J. Chem., Vol. 55, (1977), pp. 937–948. http://dx.doi.org/10.1139/v77-132[Crossref]
  • [69] C.W. Fong and H.G. Grant: “Torsional Angles inN-Substituted Benzamides and Related Compounds by Carbon-13 N.M.R. Chemical Shifts”,Aust. J. Chem., Vol. 34, (1981), pp. 957–967. http://dx.doi.org/10.1071/CH9810957
  • [70] C.W. Fong and H.G. Grant: “The Effect of Ring Size inN-Benzoyl Saturated Heterocyclic Amides”,Aust. J. Chem., Vol. 34, (1981), pp. 2307–2312. http://dx.doi.org/10.1071/CH9812307[Crossref]
  • [71] W.S. Fones, R.S. Stander and J. White: “A New Synthesis of ω-Benzoylaminovaleric Acid”,J. Org. Chem., Vol. 16, (1951), pp. 708–712. http://dx.doi.org/10.1021/jo01145a008[Crossref]
  • [72] J.L. Riebsomer: “The Synthesis of 2,3-Piperazinediones from 1,2-Diamines and Oxalic Esters”,J. Org. Chem., Vol. 15, (1950), pp. 68–73. http://dx.doi.org/10.1021/jo01147a012[Crossref]
  • [73] P.L. Southwick and R.T. Crouch: “The Condensation of Oxalic Esters with Esters of β-Alanine and N-Substituted β-Aminopropionic Acids. Synthesis of Some Derivatives of 2,3-Dioxopyrrolidine and 2-Oxo-3-methoxy-3-pyrroline”,J. Am. Chem. Soc., Vol. 75, (1953), pp. 3413–3417. http://dx.doi.org/10.1021/ja01110a034[Crossref]
  • [74] R.E. Bowman: “Experiments towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 6.N-Acyl-N-(1,2,3,4-tetrahydro-1-oxo-2-naphthyl)glycines and a New Aromatisation Reaction”,J. Chem. Soc. Perkin Trans. 1, (1983), pp. 897–901. [Crossref]
  • [75] F. Devinsky, I. Lacko, A. Nagy and L. Krasnec: “Amine oxides. I. Synthesis,1H-n.m.r., and infrared spectra of 4-alkylmorpholone-N-oxides”,Chem. Zvesti, Vol. 32, (1978), pp. 106–115.
  • [76] N. Castagnoli, Jr., J.C. Craig, A.P. Melikian and S.K. Roy: “Amine-N-oxide Rearrangements. Mechanism and Products of Thermolysis”,Tetrahedron, Vol. 26, (1970), pp. 4319–4327. http://dx.doi.org/10.1016/S0040-4020(01)93077-7[Crossref]
  • [77] T.K. Yang, S.T. Yeh and Y.Y. Lay: “Application of Electro-oxidative α-Cyanation of Aza-rings to the Synthesis of Gephyrotoxin 223AB”,Heterocycles, Vol. 38, (1994), pp. 1711–1715. http://dx.doi.org/10.3987/COM-94-6759[Crossref]
  • [78] G.F. Morris and C.R. Hauser: “Some α-Dialkylaminophenylacetonitriles and Corresponding Amino Acids and Aminoamides”,J. Org. Chem., Vol. 26, (1961), pp. 4741–4743. http://dx.doi.org/10.1021/jo01069a547[Crossref]
  • [79] A. Jonczyk, D. Lipiak and T. Zdrojewski: “Reactions of Carbanions from 2-(Dialkylamino)- arylacetonitriles with Acetylene-Simple Syntheses of 1,3-Dienamines and 1,4-Diketones”,Tetrahedron, Vol. 46, (1990), pp. 1025–1038. http://dx.doi.org/10.1016/S0040-4020(01)81381-8[Crossref]
  • [80] F.D. King and R.T. Martin: “The Synthesis of 2-Morpholine Carboxylic Acid Derivatives and Their Elaboration to 1-Aza-4-oxabicyclo[3.3.1]nonan-6-one”,Tetrahedron Lett., Vol. 32, (1991), pp. 2281–2284. http://dx.doi.org/10.1016/S0040-4039(00)79702-4[Crossref]
  • [81] C.J. Pouchert and J. Behnke:The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc., Vol. 2, No. 1432C, 1993.
  • [82] C.J. Pouchert and J. Behnke:The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc., Vol. 2, n. 932B, 1993.
  • [83] C.J. Pouchert and J. Behnke:The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc., Vol. 1, n. 1285B, 1993.
  • [84] C.J. Pouchert and J. Behnke:The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc., Vol. 2, n. 1063B., 1993.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02475575
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