Handbook of Reagents for Organic Synthesis (eBook)

Reagents for Heteroarene Synthesis

André B. Charette (Herausgeber)

eBook Download: EPUB

2017
John Wiley & Sons (Verlag)
9781118704899 (ISBN)

Infos

The Handbook is a compilation of 99 articles on diverse reagents and catalysts that describe the synthesis of heteroarenes, the building blocks of a wide range of chemicals used in pharma and chemical industries. Articles are selected from the e-EROS database and edited to make sure that it includes only the material relevant to the topic of the book and focus on the synthetic aspects. This makes the articles very focused on the needs of readers wanting information on specific syntheses of specific heteroarenes. In addition, the chemistry of each ?parent heteroarene? is also included to ensure that the reader rapidly finds important information.

The Handbook is a part of the Handbook of Reagents for Organic Chemistry series, aiming at collecting articles on a particular theme that individual researchers in academia or industry can use on a daily basis.

André B. Charette
Université de Montréal, Montréal, Canada

Inhalt

Preface ix

Introduction xi

Recent Review Articles and Monographs xiii

Short Note on InChIs and InChIKeys xvii

Acetaldoxime 1

Acetone Hydrazone 7

Acetonitrile 11

Acetonitrile N-Oxide 18

N-Aminophthalimide 19

1-Amino-pyridinium iodide 24

Ammonium Nitrate 27

Ammonium Acetate 29

Ammonium Bicarbonate 30

Benzonitrile N-Oxide 33

Benzoyl Isothiocyanate 36

N-[Bis(methylthio)methylene]-p-toluenesulfonamide 37

Bromoacetone 47

1-tert-Butyloxycarbonyl-1-methylhydrazine 52

2-Chloro-1,3-dimethylimidazolinium chloride 57

Copper(I) Chloride 61

Copper(II) Chloride 75

Copper(I) Iodide 83

Copper(II) Sulfate 93

Copper(II) Trifluoromethanesulfonate 104

Cyclopentadienylbis(triphenylphosphine)cobalt(I) 115

(Diacetoxyiodo)benzene 119

Diaminomaleonitrile 128

Diazo(trimethylsilyl)methyllithium 129

Dibromoformaldehyde Oxime 135

Dichloro Bis(acetonitrile) Palladium 137

Dichlorobis(triphenylphosphine)-palladium(II) 142

Di--chlorodichlorobis[(1,2,3,4,5-)-1,2,-3,4,5-

pentamethyl-2,4-cyclopentadien-1-yl]diiridium 146

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 172

Dichloroformaldehyde Oxime 184

Dichlorotris(triphenylphosphine)ruthenium(II) 186

(Diethoxyphosphoryl)acetonitrile oxide 191

Diethyl Oxalate 192

2,2-Difluoroethylamine 195

Diiminosuccinonitrile 199

1,3-Diisopropyl-1,3-propanedione 200

2,5-Dimethoxytetrahydrofuran 203

N,N-Dimethylacetamide Dimethyl Acetal 208

Dimethyl Diazomalonate 215

Dimethyl 2,3-Pentadienedioate 230

Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate 236

2,4-Dinitrophenylhydrazine 244

Diphenyl Cyanocarbonimidate 247

Dirhodium(II) Tetraacetate 249

Dirhodium Tetrakis(heptafluorobutyramide) 265

Di-p-tolylcarbodiimide 267

Ethyl 2-Diazo-3-oxo-3-phenylpropanoate 273

Ethyl 2-Diazo-3-oxybutyrate 275

Ethyl 2-Diazo-4,4,4-trifluoro-3-oxobutanoate 281

Ethyl Ethoxymethylenecyanoacetate 284

Formamidine Acetate 289

Gold(I) Chloride 291

Gold(III) Chloride 298

Guanidine 322

2,5-Hexanedione 327

Hydrogen Sulfide 330

Hydroxylamine 335

Indium Tribromide 343

Iodine 358

Iron(III) Bromide 374

Iron(III) Chloride 379

Malonyl Chloride 387

-Methacrolein N-tert-Butylimine 389

Methyl glycine 390

Methyl Isocyanate 393

S-Methylisothiourea 395

4-Methyloxazole 397

Methyl Thioglycolate 398

Oxo(trimanganese) Heptaacetate 401

Oxygen 402

Palladium(II) Acetate 415

Palladium(II) Chloride 449

Phenyl Isocyanide 467

Phenylhydrazine 468

Phenyliodine(III) Bis(trifluoroacetate) 472

Phosphorus Oxychloride 481

Pivalic Acid 489

Polyphosphoric Acid 497

Potassium Ethyl Xanthate 503

Potassium Monoperoxysulfate 512

Selenium(IV) Oxide 531

Semicarbazide 542

Silver(I) Hexafluoroantimonate 547

Sodium Nitrite 550

Sodium Sulfide 561

Sodium Tetrachloroaurate(III) 573

Sulfur 577

N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide

(TBBDS) 583

Tetrakis(triphenylphosphine)-palladium(0) 585

3-Thiapentanedioic acid 594

Thiourea 596

o-Tolyl Isocyanide 598

p-Tolylsulfonylmethyl isocyanide 599

Trifluomethyldiazomethane 607

Trifluoroethylamine 612

Trifluoromethanesulfonic anhydride 616

1,1,1-Trifluoro-N-phenylmethanesulfenamide 633

2-(Trimethylsilyl)phenyl Triflate 635

Triphenylphosphinegold(I) Chloride 638

List of Contributors 000

Reagent Formula Index 000

Subject Index 000

Textauszug

Recent Review Articles and Monographs

Recent Reviews

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2. Ackermann, L. Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C–H/Het–H bond functionalizations. Acc. Chem. Res. 2014, 47, 281–295.
3. Armstrong, A.; Collins, J. C. Direct azole amination: C–H Functionalization functionalization as a new approach to biologically important heterocycles. Angew. Chem., Int. Ed. 2010, 49, 2282–2285.
4. Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Synthesis of imidazo[1,2-α]pyridines: a decade update. Chem. Commun. 2015, 51, 1555–1575.
5. Barluenga, J.; Rodriguez, F.; Fananas, F. J. Recent advances in the synthesis of indole and quinoline derivatives through cascade reactions. Chem. Asian J. 2009, 4, 1036–1048.
6. Barluenga, J.; Valdes, C. Palladium catalyzed alkenyl amination: from enamines to heterocyclic synthesis. Chem. Commun. 2005, 4891–4901.
7. Bartoli, G.; Dalpozzo, R.; Nardi, M. Applications of Bartoli indole synthesis. Chem. Soc. Rev. 2014, 43, 4728–4750.
8. Batista, V. F.; Pinto, D. C. G. A.; Silva, A. M. S. Synthesis of quinolines: a green perspective. ACS Sustain. Chem. Eng. 2016, 4, 4064–4078.
9. Boyarskiy, V. P.; Ryabukhin, D. S.; Bokach, N. A.; Vasilyev, A. V. Alkenylation of arenes and heteroarenes with alkynes. Chem. Rev. 2016, 116, 5894–5986.
10. Britsun, V. N.; Esipenko, A. N.; Lozinskii, M. O. Heterocyclization of thioamides containing an active methylene group (review). Chem. Heterocycl. Compd. 2008, 44, 1429–1459.
11. Broere, D. L. J.; Ruijter, E. Recent advances in transition-metal-catalyzed [2+2+2]cyclo(co)trimerization reactions. Synthesis 2012, 44, 2639–2672.
12. Cacchi, S.; Fabrizi, G. Update 1 of: Synthesis and functionalization of indoles through palladium-catalyzed reactions. Chem. Rev. 2011, 111, PR215–PR283.
13. Cavitt, M. A.; Phun, L. H.; France, S. Intramolecular donor–acceptor cyclopropane ring-opening cyclizations. Chem. Soc. Rev. 2014, 43, 804–818.
14. Chopade, P. R.; Louie, J. [2+2+2] cycloaddition Cycloaddition reactions catalyzed by transition metal complexes. Adv. Synth. Catal. 2006, 348, 2307–2327.
15. Ciufolini, M. A.; Chan, B. K. Methodology for the synthesis of pyridines and pyridones: Development development and applications. Heterocycles 2007, 74, 101–124.
16. Dhakshinamoorthy, A.; Garcia, H. Metal-organic frameworks as solid catalysts for the synthesis of nitrogen-containing heterocycles. Chem. Soc. Rev. 2014, 43, 5750–5765.
17. D'Souza, D. M.; Muller, T. J. J. Multi-component syntheses of heterocycles by transition-metal catalysis. Chem. Soc. Rev. 2007, 36, 1095–1108.
18. Egi, M.; Akai, S. Transition metal-catalyzed intramolecular cyclization of propargyl alcohols and their derivatives for the synthesis of highly substituted five-membered oxygen heterocycles. Heterocycles 2015, 91, 931–958.
19. El-Taweel, F. M. A.; Abou Elmaaty, T. M. Synthetic routes to selected heterocycles containing antipyrine moiety. J. Heterocycl. Chem. 2016, 53, 677–684.
20. Estevez, V.; Villacampa, M.; Menendez, J. C. Multicomponent reactions for the synthesis of pyrroles. Chem. Soc. Rev. 2010, 39, 4402–4421.
21. Estevez, V.; Villacampa, M.; Menendez, J. C. Recent advances in the synthesis of pyrroles by multicomponent reactions. Chem. Soc. Rev. 2014, 43, 4633–4657.
22. Fairlamb, I. J. S. Regioselective (site-selective) functionalisation of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes. Chem. Soc. Rev. 2007, 36, 1036–1045.
23. Fang, G. C.; Bi, X. H. Silver-catalysed reactions of alkynes: recent advances. Chem. Soc. Rev. 2015, 44, 8124–8173.
24. Foster, R. A. A.; Willis, M. C. Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis. Chem. Soc. Rev. 2013, 42, 63–76.
25. Gouda, M. A. Utility of 3-Aminoamino-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine in heterocyclic synthesis. J. Heterocyclic Heterocycl. Chem. 2011, 48, 1–10.
26. Hassan, A. A.; El-Sheref, E. M.; Abou-Zied, A. H. Heterocyclization of acylthiosemicarbazides. J. Heterocyclic Heterocycl. Chem. 2012, 49, 38–58.
27. Heller, B.; Hapke, M. The fascinating construction of pyridine ring systems by transition metal-catalysed [2+2+2] cycloaddition reactions. Chem. Soc. Rev. 2007, 36, 1085–1094.
28. Henry, G. D. De novo synthesis of substituted pyridines. Tetrahedron 2004, 60, 6043–6061.
29. Heugebaert, T. S. A.; Roman, B. I.; Stevens, C. V. Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles. Chem. Soc. Rev. 2012, 41, 5626–5640.
30. Hua, Y. R.; Flood, A. H. Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry. Chem. Soc. Rev. 2010, 39, 1262–1271.
31. Janin, Y. L. Preparation and Chemistry chemistry of 3/5-halogenopyrazoles. Chem. Rev. 2012, 112, 3924–3958.
32. Kamijo, S.; Yamamoto, Y. Recent progress in the catalysis synthesis in imidazoles. Chem. –Asian J. 2007, 2, 568–578.
33. Kaur, T.; Wadhwa, P.; Bagchi, S.; Sharma, A. Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs). Chem. Commun. 2016, 52, 6958–6976.
34. Keiko, N. A.; Vchislo, N. V. Synthesis of imidazo[1,2-a]pyridines from alpha,beta-unsaturated aldehydes (microreview). Chem. Heterocycl. Compd. 2016, 52, 222–224.
35. Kruger, K.; Tillack, A.; Beller, M. Catalytic Synthesis synthesis of Indoles indoles from Alkynesalkynes. Adv. Synth. Catal. 2008, 350, 2153–2167.
36. Maji, P. K.; Ul Islam, R.; Bera, S. K. Recent progress in metal assisted multicomponent syntheses of heterocycles. Heterocycles 2014, 89, 869–962.
37. Majumdar, K. C.; Debnath, P.; Roy, B. Metal-catalyzed heterocyclization: formation of five-and six-membered oxygen heterocycles through carbon–oxygen bond forming reactions. Heterocycles 2009, 78, 2661–2728.
38. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. The aza-Wittig reaction: an efficient tool for the construction of carbon–nitrogen double bonds. Tetrahedron 2007, 63, 523–575.
39. Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Recent Developments developments in the Synthesis synthesis of Imidazoimidazo[1,2-a]pyridines. Synthesis 2015, 47, 887–912.
40. Rossi, R.; Bellina, F.; Lessi, M.; Manzini, C.; Perego, L. A. Synthesis of multiply arylated heteroarenes, including bioactive derivatives, via palladium-catalyzed direct C–H arylation of heteroarenes with (pseudo)aryl halides or aryliodonium salts. Synthesis 2014, 46, 2833–2883.
41. Ruiz-Castillo, P.; Buchwald, S. L. Applications of palladium-catalyzed C–N cross-coupling reactions. Chem. Rev. 2016, 116, 12564–12649.
42. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. 2-aminothiophenes Aminothiophenes by the Gewald reaction. J. Heterocyclic Heterocycl. Chem. 1999, 36, 333–345.
43. Sadig, J. E. R.; Willis, M. C. Palladium-and copper-catalyzed aryl halide amination, etherification and thioetherification reactions in the synthesis of aromatic heterocycles. Synthesis 2011, 1–22.
44. Serrano-Molina, D.; Martin-Castro, A. M. Tandem sequences involving michael Michael additions and sigmatropic rearrangements. Synthesis 2016, 48, 3459–3469.
45. Shestopalov, A. M.; Shestopalov, A. A.; Rodinovskaya, L. A. Multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid: Synthesis synthesis of carbo-and heterocycles. Synthesis 2008, 1–25.
46. Taber, D. F.; Tirunahari, P. K. Indole synthesis: a review and proposed classification. Tetrahedron 2011, 67, 7195–7210.
47. Tanaka, K. Rhodium-Catalyzed catalyzed [2+2+2] Cycloaddition cycloaddition for the synthesis of substituted pyridines, pyridones, and thiopyranimines. Heterocycles 2012, 85, 1017–1043.
48. Thirumalairajan, S.; Pearce, B. M.; Thompson, A. Chiral molecules containing the pyrrole framework. Chem. Commun. 2010, 46, 1797–1812.
49. Wang, Y. L.; Zhang, L. M. Recent developments in the chemistry of heteroaromatic N-Oxidesoxides. Synthesis 2015,...

Produkt-Details

• Erscheint lt. Verlag: 31.5.2017
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Naturwissenschaften ► Chemie ► Physikalische Chemie
• Schlagworte: Chemie • Chemistry • heteroarenes heterocycles synthesis reagents catalysts reaction conditions safety purification storage • Heteroaromaten • Methods - Synthesis & Techniques • Natural Products • Naturstoffchemie • Organische Chemie • Organische Chemie / Methoden, Synthesen, Verfahren • Pharmaceutical & Medicinal Chemistry • Pharmazeutische u. Medizinische Chemie
• ISBN-13: 9781118704899 / 9781118704899