Pyridine elaboration through organometallic intermediates: regiochemical control and completeness.
暂无分享,去创建一个
[1] Ann Thayer,et al. Enzymes at Work , 2006, Science.
[2] M. Schlosser. CF3-substituierte aromatische und heterocyclische Bausteine , 2006 .
[3] F. Wagner,et al. Regioselective 5-, 4-, and 2-Substitution of (S)-6-Chloronicotine and 4-Substitution of (S)-5-Chloronicotine , 2006 .
[4] P. Gros,et al. TMSCH2Li–LiDMAE: a new nonnucleophilic reagent for C-2 lithiation of halopyridines , 2006 .
[5] A. Thayer. CONSTRUCTING LIFE SCIENCES COMPOUNDS , 2006 .
[6] D. Comins,et al. Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives. , 2005, Organic letters.
[7] M. Schlosser,et al. Converting core compounds into building blocks : The concept of regiochemically exhaustive functionalization , 2005 .
[8] M. Schlosser,et al. Selective functionalization of 2-fluoropyridine, 2,3-difluoropyridine, and 2,5-difluoropyridine at each vacant position. , 2005, The Journal of organic chemistry.
[9] M. Schlosser,et al. Removal of fluorine from and introduction of fluorine into polyhalopyridines: an exercise in nucleophilic hetarenic substitution. , 2005, Chemistry.
[10] M. Schlosser,et al. Regiochemically flexible substitutions of di-, tri-, and tetrahalopyridines: the trialkylsilyl trick. , 2005, The Journal of organic chemistry.
[11] M. Schlosser. Der 2×3‐Werkzeugkasten der metallorganischen Methoden zur regiochemisch erschöpfenden Funktionalisierung , 2005 .
[12] M. Schlosser,et al. Rerouting nucleophilic substitution from the 4-position to the 2- or 6-position of 2,4-dihalopyridines and 2,4,6-trihalopyridines: the solution to a long-standing problem. , 2005, Organic letters.
[13] M. Schlosser,et al. Logistic flexibility in the preparation of isomeric halopyridinecarboxylic acids , 2004 .
[14] M. Schlosser,et al. Three Chloro(trifluoromethyl)pyridines as Model Substrates for Regioexhaustive Functionalization , 2004 .
[15] M. Schlosser,et al. Regioflexibility in the Functionalization of Multiply Halogenated Quinolines , 2004 .
[16] M. Schlosser,et al. The Structural Proliferation of 2,6‐Difluoropyridine through Organometallic Intermediates , 2004 .
[17] M. Schlosser,et al. Exploring Structural Opportunities: The Regioflexible Substitution of 1,3‐Difluorobenzene , 2003 .
[18] P. Gros,et al. Side-Chain Retention During Lithiation of 4-Picoline and 3,4-Lutidine: Easy Access to Molecular Diversity in Pyridine Series , 2003 .
[19] M. Schlosser,et al. Recommendable Routes to Trifluoromethyl‐Substituted Pyridine‐ and Quinolinecarboxylic Acids , 2003 .
[20] M. Schlosser,et al. The Direct Metalation and Subsequent Functionalization of Trifluoromethyl‐Substituted Pyridines and Quinolines , 2003 .
[21] P. Gros,et al. nBuLi/Lithium Aminoalkoxide Aggregates: New and Promising Lithiating Agents for Pyridine Derivatives , 2002 .
[22] F. Mongin,et al. Directed lithiation of unprotected pyridinecarboxylic acids: syntheses of halo derivatives , 2002 .
[23] T. Hiyama. How I came across the silicon-based cross-coupling reaction , 2002 .
[24] P. Gros,et al. Ring Selective Lithiation of 3,5-Lutidine. A New Route to Heterocyclic Building Blocks. , 2002 .
[25] M. Schlosser,et al. Trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper , 2002 .
[26] M. Schlosser,et al. Regiochemical Flexibility: The Optional Functionalization of 2,3,5‐Trihalopyridines at the 4‐ or 6‐Position , 2001 .
[27] M. Schlosser,et al. Strategies for the Selective Functionalization of Dichloropyridines at Various Sites , 2001 .
[28] M. Schlosser,et al. Multiple hydrogen/lithium interconversions at the same benzene nucleus: two at the most. , 2001, Journal of the American Chemical Society.
[29] P. Gros,et al. First Regioselective C‐2 Lithiation of 3‐ and 4‐Chloropyridines , 2001 .
[30] L. Yagupolskii,et al. N-Trihalomethyl derivatives of benzimidazole, benzotriazole and indazole , 2000 .
[31] Choppin,et al. Unusual C-6 Lithiation of 2-Chloropyridine-Mediated by BuLi-Me(2)N(CH(2))(2)OLi. New Access to 6-Functional-2-chloropyridines and Chloro-bis-heterocycles. , 2000, Organic letters.
[32] A. Rees,et al. Preparation and reactions of 2,3,4,6-tetrafluoropyridine and its derivatives , 2000 .
[33] P. Knochel,et al. BROMINE-MAGNESIUM-EXCHANGE AS A GENERAL TOOL FOR THE PREPARATION OF POLYFUNCTIONAL ARYL AND HETEROARYL MAGNESIUM-REAGENTS , 1999 .
[34] F. Mongin,et al. Directed lithiation of unprotected pyridinecarboxylic acids , 1999 .
[35] V. Bonnet,et al. Pyridylmagnesium chlorides from bromo and dibromopyridines by brominemagnesium exchange: A convenient access to functionalized pyridines , 1999 .
[36] Y. Kondo,et al. TMP−Zincate as Highly Chemoselective Base for Directed Ortho Metalation , 1999 .
[37] C. Holzapfel,et al. CROSS COUPLING STRATEGIES TOWARDS THE SYNTHESIS OF THE STREPTONIGRIN CD MOIETY , 1999 .
[38] J. Paris,et al. Reactivity of 1-(des-3-hydroxy-picolinoyl) pristinamycin IA , 1998 .
[39] D. J. Moody,et al. ELECTROPHILIC IPSO SUBSTITUTION OF TRIMETHYLSILYL GROUPS IN FLUOROBENZENES , 1998 .
[40] P. Gros,et al. Aggregative activation in heterocyclic chemistry. Part 6.† A surprising NH3 effect during metallation of 2-methoxypyridine with a multimetal complex base: C-3 versus C-6 metallation , 1998 .
[41] R. Chambers,et al. Polyhalogenated heterocyclic compounds. Part 42.1 Fluorinated nitrogen heterocycles with unusual substitution patterns , 1998 .
[42] A. Chan,et al. New Rhodium Pyridylphosphine Complexes and Their Application in Hydrogenation Reactions , 1997 .
[43] Paramjit Singh,et al. Lewis Acid Complexation of Tertiary Amines and Related Compounds: A Strategy for alpha-Deprotonation and Stereocontrol. , 1997, Chemical reviews.
[44] C. Avendaño,et al. A NEW MODIFICATION OF THE FRIEDLANDER SYNTHESIS VIA ORTHO-DILITHIATED N-PIVALOYLANILINES , 1997 .
[45] P. Gros,et al. Aggregative activation in heterocyclic chemistry. Part 4. Metallation of 2-methoxypyridine: unusual behaviour of the new unimetal superbase BuLi–Me2N(CH2)2OLi (BuLi–LiDMAE) , 1997 .
[46] P. Gros,et al. Aggregative activation in heterocyclic chemistry. Part 5.† Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE) , 1997 .
[47] M. Schlosser,et al. About bases and superbases , 1997 .
[48] J. Zoltewicz,et al. Inter-ring directed ortho lithiation by the 2-pyridyl group in bipyridines , 1996 .
[49] F. Marsais,et al. Synthesis of new pyridine intermediates as precursors for the elaboration of streptonigrin analogues by the metalation-cross-coupling strategy , 1996 .
[50] M. Schlosser,et al. Optional Site Selectivity in the Metalation of o- and p-Anisidine through Matching of Reagents with Neighboring Groups , 1996 .
[51] D. Hands,et al. A Convenient Method for the Preparation of 5-, 6- and 7-Azaindoles and Their Derivatives , 1996 .
[52] E. Bayburt,et al. Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine , 1996 .
[53] E. Vedejs,et al. Kinetic Resolution of Secondary Alcohols. Enantioselective Acylation Mediated by a Chiral (Dimethylamino)pyridine Derivative , 1996 .
[54] P. Gros,et al. Aggregative activation and heterocyclic chemistry III. Unusual regioselective lithiation of 2-alkoxy-pyridines , 1995 .
[55] M. Schlosser,et al. Metalated fluoropyridines and fluoroquinolines as reactive intermediates: new ways for their regioselective generation , 1994 .
[56] M. Schlosser,et al. Site selective hydrogen/metal exchange: Competition and cooperation between superbases and neighboring groups , 1994 .
[57] W. Dmowski,et al. Reactions of trifluoromethylpyridines with alkyllithium reagents. Directing effects of the trifluoromethyl groups , 1994 .
[58] P. Caubére. Unimetal super bases , 1993 .
[59] G. Gribble,et al. Regioselective ortho-Lithiation of Halopyridines. Syntheses of ortho-Disubstituted Pyridines and a Convenient Generations of 3,4-Pyridyne , 1993 .
[60] M. Schlosser,et al. A shortcut to α-Santalol , 1993 .
[61] O. Mongin,et al. New synthesis of Orelline by metalation of methoxypyridines , 1993 .
[62] D. Comins. The Synthetic Utility of α-Amino Alkoxides , 1993 .
[63] J. Bourguignon,et al. Metalation of pi-deficient heterocycles a facile synthesis of cerpegin , 1992 .
[64] D. Comins,et al. N-acyldihydropyridones as synthetic intermediates. synthesis of (±)-septicine and (±)-tylophorine. , 1991 .
[65] F. Effenberger,et al. Darstellung von Didehydropyridinen aus (Trimethylsilyl)pyridinen , 1991 .
[66] M. Schlosser,et al. A one-pot synthesis of ibuprofene involving three consecutive steps of superbase metalation , 1991 .
[67] M. Khaimova,et al. Lithiation of polychloropyrimidines and dichloropyridines , 1991 .
[68] Paramjit Singh,et al. Lewis acid complexed heteroatom carbanions; synthesis of some α-pyridyl alcohols , 1991 .
[69] M. Schlosser,et al. The metalation of fluoroanisoles: optional regioselectivity due to metal mediated control , 1991 .
[70] D. Comins,et al. Lithiation of methoxypyridines directed by .alpha.-amino alkoxides , 1990 .
[71] C. A. Leonard,et al. Benzo- and pyrido-1,4-oxazepin-5-ones and -thiones: synthesis and structure-activity relationships of a new series of H1 antihistamines. , 1989, Journal of medicinal chemistry.
[72] A. Bieniek,et al. Application of organolithium and related reagents in synthesis. Part 7. Synthesis and metallion of 4-methoxypicolin- and 2-methoxyisonicotin-anilides. A useful method for preparation of 2, 3, 4-trisubstituted pyridines , 1989 .
[73] M. Venuti,et al. Inhibitors of cyclic AMP phosphodiesterase. 3. Synthesis and biological evaluation of pyrido and imidazolyl analogues of 1,2,3,5-tetrahydro-2-oxoimidazo[2,1-b]quinazoline. , 1988, Journal of medicinal chemistry.
[74] S. Kafafi,et al. Carbon acidities of aromatic compounds. 1. Effects of in-ring aza and external electron-withdrawing groups , 1988 .
[75] F. Marsais,et al. Metalation/SRN1 coupling in heterocyclic synthesis. A convenient methodology for ring functionalization , 1988 .
[76] J. Falck,et al. A Convenient Synthesis of Pyrido[3,4-g]isoquinoline via ortho-Directed Metallation/Dimerization , 1988 .
[77] F. Marsais,et al. Catalyzed metalation applied to 2-methoxypyridine , 1988 .
[78] M. Schlosser. Superbases for organic synthesis , 1988 .
[79] D. W. Strickland,et al. Synthesis of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,6-naphthyridines by a directed lithiation reaction , 1988 .
[80] F. Marsais,et al. Directed lithiation of 4-halopyridines: Chemoselectivity, regioselectivity and application to synthesis , 1988 .
[81] E. Knaus,et al. An improved synthesis of 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido[3,4-e]-1,4-diazepin-2-one via ortho-directed lithiation of 3-tert-butyl and 3-tert-butoxycarbonylaminopyridine , 1987 .
[82] G. Olah,et al. Desilylative nitration of alkyl- and allylsilanes with nitronium salts , 1987 .
[83] A. Bell,et al. A Direct Synthesis of 6-Pyridinyl-2(1H)-quinolinones via Palladium-Catalysed Cross-Coupling Reaction , 1987 .
[84] E. Bisagni,et al. A new route to [g]-fused 5-methyl-1-functionalized isoquinolines , 1987 .
[85] M. Iwao,et al. Synthesis of bostrycoidin via directed lithiation of tertiary nicotinamide , 1987 .
[86] H. Fujihara,et al. Preparation of pyridyl grignard reagents and cross coupling reactions with sulfoxides bearing azaheterocycles , 1987 .
[87] L. W. Sieck,et al. Relative acidities of water and methanol and the stabilities of the dimer anions , 1986 .
[88] E. Thomas. Synthesis of indolizinones and a pyridoazepinone: a new method for the annulation of pyridinones , 1986 .
[89] M. Haimova,et al. Synthesis of 4-Amino-3-pyridinyl and 4-Amino-5-pyrimidinyl Aryl Ketones and Related Compounds via an ortho-Lithiation Reaction , 1986 .
[90] M. Mallet,et al. Action du n-butyllithium sur les bromo-3 halogeno-2 pyridines fluoree, chloree et bromee : Principe et etude d'une possibilite reactionnelle nouvelle : l'homotransmetallation , 1985 .
[91] L. Brandsma,et al. Kinetic and thermodynamic control in the metalation of pyridine. A direct synthesis of 2-and 4-substituted pyridines , 1984 .
[92] M. Ishikura,et al. Total synthesis of SEN-215 by use of palladium catalyzed carbonylation , 1984 .
[93] K. Akiba,et al. A Convenient Method for the Regioselective Synthesis of 4-Alkyl(aryl)pyridines Using Pyridinium Salts , 1984 .
[94] L. Brandsma,et al. Functionalization of pyridine via direct metallation , 1984 .
[95] M. Schlosser,et al. The “super-basic” butyllithium/potassium tert-butoxide mixture and other lickor-reagents , 1984 .
[96] T. Mano,et al. AN ALTERNATIVE SYNTHESIS OF DIALKYLPYRIDYLBORANES , 1984 .
[97] J. C. Martin,et al. Direct, regiospecific 2-lithiation of pyridines and pyridine 1-oxides with in situ electrophilic trapping , 1983 .
[98] J. A. Turner. Regiospecific electrophilic substitution of aminopyridines: ortho lithiation of 2-, 3-, and 4-(pivaloylamino)pyridines , 1983 .
[99] J. C. Martin,et al. In situ trapping of ortho lithiated benzenes containing electrophilic directing groups , 1983 .
[100] M. Iwao,et al. Synthesis of (±)-sesbanine via directed metalation of tertiary nicotinamides , 1983 .
[101] R. Ronald,et al. Regioselective metallations of (methoxymethoxy)arenes , 1983 .
[102] F. Marsais,et al. Review on the metallation of π -deficient heteroaromatic compounds , 1983 .
[103] K. Akiba,et al. Facile synthesis of 4-substituted pyridines using grignard reagents , 1983 .
[104] T. Güngör,et al. ortho-Functionalization of Aminopyridines; Regioselective Lithiation of 3-Pivaloylaminopyridines , 1982 .
[105] F. Marsais,et al. Regioselective o-Lithiation of 3-Alkoxypyridines; A Convenient Route to New o-Disubstituted Pyridines , 1982 .
[106] R. Gabel,et al. Substitutions of pyridines activated by oxazolines via nucleophilic additions for metalation-alkylation , 1982 .
[107] R. Ronald,et al. Regioselective metalation reactions of some substituted (methoxymethoxy)arenes , 1982 .
[108] M. Mallet,et al. Reaction de la bromo-3 pyridine avec le diisopropylamidure de lithium. Mecanismes de metallation et de migration d'halogene. Regioselectivite de l'addition polaire sur la pyridyne-3,4 , 1982 .
[109] G. Quéguiner,et al. Etude des ortho-metallations regioselectives de la chloro-3 pyridine par des organolithiens et des amidures de lithium; effet d'orientation par le solvant, applications a la synthese , 1981 .
[110] Y. Kita,et al. Regioselective metalation of the 4-position of pyridine. New and convenient alkylation and acylation of 3-amino-5-methoxypyridine , 1981 .
[111] A. Katritzky,et al. 3-Lithiated Pyridines and their Reactions with Electrophiles , 1981 .
[112] G. Gribble,et al. Regioselective ortho lithiation of halopyridines , 1981 .
[113] M. Venuti,et al. Ortho functionalization of N-(tert-butoxycarbonyl)aniline , 1980 .
[114] J. Brzezinski,et al. Reactions of the N,N-dialkylpyridylcarboxylic amides with lithium amides. Regioselective lithiation of N,N-diisopropylpyridylcarboxylic amides, a useful method for synthesis of 2,3- and 3,4-disubstituted pyridines☆ , 1980 .
[115] J. Olah,et al. Synthetic methods and reactions. 63. Pyridinium poly(hydrogen fluoride) (30% pyridine-70% hydrogen fluoride): a convenient reagent for organic fluorination reactions , 1979 .
[116] R. Gabel,et al. Oxazolines as activating groups in aromatic substitution. Regioselective metallation of the 3-position in pyridine. , 1978 .
[117] I. Vlattas,et al. LITHIATION OF 4,4-DIMETHYL-2-(2-THIENYL)-2-OXAZOLINE , 1977 .
[118] P. Beak,et al. THE ORTHO LITHIATION OF TERTIARY BENZAMIDES , 1977 .
[119] H. Gschwend,et al. Ortho-lithiation. A regiospecific route to ortho-substituted aryl ketones , 1976 .
[120] C. D. Weis,et al. Halogenierte Pyridine II. Reaktionen der 3‐Halogenmethyl‐pyridine , 1976 .
[121] C. Eaborn. Cleavages of aryl-silicon and related bonds by electrophiles , 1975 .
[122] W. Paudler,et al. CATALYTIC REDUCTION OF 4-NITROPYRIDINE 1-OXIDE , 1975 .
[123] R. Abramovitch,et al. The direct thionation and aminoalkylation of pyridine 1-oxides and related reactions† , 1975 .
[124] A. Hamdan,et al. Ortho-lithiation of aryloxazolines , 1975 .
[125] B. Wakefield,et al. Polyhalogenoaromatic compounds : XXIX. Hexachloro-5,5′-dilithio-4,4′-bipyridine as an intermediate for organometallic and organic syntheses , 1974 .
[126] O. Meth–Cohn,et al. Novel aspects of the metalation of heterocycles. Side-chain metalation of thiophen and ring metalation of six-membered nitrogen heterocycles , 1974 .
[127] M. Schlosser,et al. Ummetallierung und doppelter Metall-Austausch: ein bequemer Zugang zu Organolithium-Verbindungen vom Benzyl- und Allyl-Typ , 1973 .
[128] R. Abramovitch,et al. Direct acylamination of pyridine 1-oxides , 1972 .
[129] A. Katritzky,et al. The kinetics and mechanism of electrophilic substitution of heteroaromatic compounds. Part XX. Nitration of 3-hydroxypyridine, 6-hydroxy-2(1H)-pyridone, and some corresponding methyl derivatives , 1970 .
[130] S. Taguchi,et al. Studies on Organic Fluorine Compounds. VI. Preparations and Reactions of (Trifluoromethyl) quinoline N-Oxides , 1969 .
[131] C. A. Heaton,et al. Polyfluoroheterocyclic compounds. Part XVI. Tetrafluoropyridine-3- and -4-carbaldehydes and some derivatives of the latter , 1969 .
[132] M. Schlosser. Zur aktivierung lithiumorganischer reagenzien , 1967 .
[133] E. Smith,et al. A New and Convenient Alkylation and Acylation of Pyridine N-Oxides , 1967 .
[134] A. Katritzky,et al. The mechanism of the electrophilic substitution of heteroaromatic compounds. Part VIII. The α-, β-, and γ-nitration of pyridine 1-oxides , 1967 .
[135] R. Chambers,et al. 926. Polyfluoroheterocyclic compounds. Part V. Catalytic reduction of perfluoro- and chlorofluoro-pyridines and the preparation of polyfluoropyridinecarboxylic acids , 1965 .
[136] C. Hauser,et al. Metalation of N-Methylbenzamide with Excess n-Butyllithium. Condensations with Electrophilic Compounds to Form ortho Derivatives. Cyclizations1 , 1964 .
[137] A. F. Crowther. Heterocyclic Chemistry , 1964, Nature.
[138] M. S. Raasch. The Chemistry of Sulfur Tetrafluoride. IX. Reaction with Amino Acids in Hydrogen Fluoride1 , 1962 .
[139] W. Hasek,et al. The Chemistry of Sulfur Tetrafluoride. II. The Fluorination of Organic Carbonyl Compounds1 , 1960 .
[140] A. Katritzky,et al. 248. N-oxides and related compounds. Part X. The hydrogenation of some pyridine 1-oxides , 1958 .
[141] F. Leonard,et al. Synthesis of Some Sulfur-Containing Derivatives of Pyridine 1-Oxide and Quinoline 1-Oxide , 1956 .
[142] J. A. Berson,et al. SYNTHETIC APPROACHES TO IPECAC ALKALOIDS. II. A SYNTHESIS OF 4-CARBOMETHOXY-5-ETHYL-2-METHYLPYRIDINE1, 2 , 1955 .
[143] E. Ochiai. RECENT JAPANESE WORK ON THE CHEMISTRY OF PYRIDINE 1-OXIDE AND RELATED COMPOUNDS , 1953 .
[144] H. French,et al. Some Reactions of 3-Pyridyllithium1 , 1951 .
[145] Scherer. Über organische Fluorverbindungen , 1939 .
[146] J. Simons,et al. The Preparation of Benzotrifluoride , 1938 .
[147] A. Kirpal,et al. Über eine neuartige Isomerie in der Pyridin‐Reihe (I. Mitteil.) , 1932 .
[148] A. Kirpal,et al. Über 2‐Nitro‐pyridin. (Vorläufige Mitteilung) , 1931 .
[149] K. Ziegler,et al. Untersuchungen über alkaliorganische Verbindungen, VII. Mitteil.: Alkalimetallalkyle und Pyridin (Vorläufige Mitteilung) , 1930 .