Recent advances in synthesis of ketenimines
Tài liệu tham khảo
Aumann, 1988, Ketenimine Complexes from Carbene Complexes and Isocyanides: Versatile Building Blocks for Carbocycles and N-Heterocycles [New Synthetic Methods, Angew. Chem. Int. Ed. Engl., 27, 1456, 10.1002/anie.198814561
Alajarin, 2012, Recent Highlights in Ketenimine Chemistry, Eur. J. Org. Chem., 29, 5637, 10.1002/ejoc.201200383
Alajarin, 1996, Intramolecular [2 + 2] cycloaddition of ketenimines with imines, Tetrahedron Lett., 37, 8945, 10.1016/S0040-4039(96)02054-0
Aumann, 1988, Keteniminkomplexe aus Carbenkomplexen und Isocyaniden – vielseitige Bausteine für Carbocyclen und N-Heterocyclen, Angew Chem., 100, 1512, 10.1002/ange.19881001106
Alajarin, 2000, Periselective intramolecular [4+2] cycloadditions of ketenimines: synthesis of pyrido[1,2-a] benzimidazoles, Tetrahedron Lett., 41, 7029, 10.1016/S0040-4039(00)01197-7
Ariyaratne, 1963, Some ketenimine complexes of iron, J. Chem. Soc., 2976, 10.1039/jr9630002976
Alajarin, 2012, Tandem [1,5]-H shift/6p-electrocyclizations of ketenimines bearing 1,3-oxathiane units. Computational assessment of the experimental diastereoselection, Tetrahedron Lett., 68, 4672, 10.1016/j.tet.2012.04.021
Anaraki-Ardakani, 2011, Three-component synthesis of dialkyl 2-(cyclohexyliminomethylene)-3-arylsulfonylamino succinate, J. Chem. Res., 35, 98, 10.3184/174751911X12964930076881
Asghari, 2013, One-pot synthesis of N-substituted 2,4-thiazolidinediones and computational investigation of the products, Monatsh. Chem., 144, 337, 10.1007/s00706-012-0815-4
Alexander, 2017, Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π–Allylic Rearrangement of N-Alloc Ynamides, Org. Lett., 19, 5822, 10.1021/acs.orglett.7b02780
Alajarin, 2004, Imino-Ketenimines on an Ortho-Benzylic Scaffold. Nitrogen to Carbon [1,3] Shift of an Ortho-Functionalized Benzyl Group, Lett. Org. Chem., 1, 340, 10.2174/1570178043400398
Borrmann, 1968
Beck, 1966, Über Metall-Stickoxid-Komplexe. XXI. Tricyanomethanido–Nitrosyl-Komplexe von Kobalt und Nickel, Z. Anorg. Allg. Chem., 344, 285, 10.1002/zaac.19663440508
Beck, 1967, Pseudohalogeno—Metallverbindungen XVIII. Anionische (Tricyanomethanido)pentacarbonyl-Komplexe von Chrom, Molybdän und Wolfram, J. Organometal. Chem., 8, 547, 10.1016/S0022-328X(00)83678-5
Barker, 1972, Heterocycles from ketenimines. V. 2-Iminoazetidines through thermolysis, J. Heterocyclic Chem., 9, 1147, 10.1002/jhet.5570090535
Bayat, 2008, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, Synth. Commun., 38, 2567, 10.1080/00397910802219213
Bissember, 2018, α-Cyanocarbanion complexes and their application in synthesis, J. Organomet. Chem., 869, 213, 10.1016/j.jorganchem.2018.04.010
Bendikov, 2005, An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement, Org. Lett, 7, 783, 10.1021/ol0477327
Corey, 1995
Cheng, 2009, An Unprecedented Chemospecific and Stereoselective Tandem Nucleophilic Addition/Cycloaddition Reaction of Nucleophilic Carbenes with Ketenimines, J. Org. Chem., 74, 850, 10.1021/jo802289s
Coffinier, 2011, A new multicomponent reaction for the synthesis of pyridines via cycloaddition of azadienes and ketenimines, Tetrahedron Lett., 52, 3023, 10.1016/j.tetlet.2011.04.007
Clarke, 1992, Relatively Stable N-Benzhydryl- and N-Benzyldiarylketene Imines and Their Conversion to Cyanodiarylmet hanes via an Isolable Radical, Org. Chem., 57, 362, 10.1021/jo00027a062
Dodd, 2018, Ketenimines Generated from Ynamides: Versatile Building Blocks for Nitrogen-Containing Scaffolds, Chem. Eur. J., 24, 2297, 10.1002/chem.201704689
Dijkstra, 1954, Imenes derived from methylsulphonyl-acetonitrile: (Properties of the sulphonyl group XLIII), Recl. Trav. Chim. Pays-Bas., 73, 575, 10.1002/recl.19540730710
Denmark, 2012, Silyl Ketene Imines: Highly Versatile Nucleophiles for Catalytic, Asymmetric Synthesis, Angew. Chem. Int. Ed., 51, 9980, 10.1002/anie.201202139
Domling, 2006, Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry, Chem. Rev., 106, 17, 10.1021/cr0505728
Dos Santos, 2017, Nef–Perkow–Mumm Cascade towards Imido Phosphate Derivatives, Synlett, 28, 2637, 10.1055/s-0036-1590856
Dwyer, 1999, An asymmetric oxazoline ketenimine rearrangement. Construction of chiral o -quaternary carbon ketones, Tetrahedron Lett., 40, 4765, 10.1016/S0040-4039(99)00729-7
De Korver, 2010, A Divergent Mechanistic Course of Pd(0)-Catalyzed Aza-Claisen Rearrangement and Aza-Rautenstrauch-Type Cyclization of N-Allyl Ynamides, Org. Lett., 12, 1840, 10.1021/ol100446p
De Korver, 2011, N-Allyl-N-sulfonyl Ynamides as Synthetic Precursors to Amidines and Vinylogous Amidines. An Unexpected N-to-C 1,3-Sulfonyl Shift in Nitrile Synthesis, J. Org. Chem, 76, 5092, 10.1021/jo200780x
Doney, 1983, New Donors with Two-Electron Oxidation. Synthesis and Electrochemical Properties of Highly Conjugated Bis(4H-pyrans), Bis(4H-thiopyrans), and Bis(flavenes), J. Org. Chem., 4, 2757
Dekorver, 2010, A Divergent Mechanistic Course of Pd (0)-Catalyzed Aza-Claisen Rearrangement and Aza-Rautenstrauch-Type Cyclization of N-Allyl Ynamides, Org. Lett., 12, 1840, 10.1021/ol100446p
Dekorver, 2012, Carbocyclization Cascades of Allyl Ketenimines via Aza-Claisen Rearrangements of N-Phosphoryl-N-allyl-ynamide, Org. Lett., 14, 1768, 10.1021/ol300366e
Falmagne, 1981, Cyclobutanone and Cyclobutenone Derivatives by Reaction of Tertiary Amides with Alkenes or Alkynes, Angew. Chem. Int., 20, 879, 10.1002/anie.198108791
Fedushkin, 2009, Magnesium (II) Complexes of the dpp-BIAN Radical-Anion: Synthesis, Molecular Structure, and Catalytic Activity in Lactide Polymerization, Eur. J. Inorg. Chem., 2009, 4995, 10.1002/ejic.200900710
Groult, 2017
Gambaryan, 1976, Fluorinated Ketenimines, Russ. Chem. Rev., 45, 630, 10.1070/RC1976v045n07ABEH002698
Guan, 2019, One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction, Synth., 51, 2402, 10.1055/s-0037-1612279
Grass, 2019, Ketenimine Formation Catalyzed by a High-Valent Cobalt Carbene in Bulky Alkoxide Ligand Environment, J. Organomet. Chem., 38, 962, 10.1021/acs.organomet.8b00911
Guérin, 2020, Synthesis and use of trifluoromethylthiolated ketenimines, Chem. Eur. J., 26, 14852, 10.1002/chem.202002723
Haufe, 2019
Hiroi, 1985, Asymmetric Induction Reactions. I. Asymmetric [2, 3] Sigmatropic Rearrangements of Sulfur Ylides Derived from Chiral Ketenimines and Trimethylsulfonium YlideChem, Pharm. Bull., 33, 2331, 10.1248/cpb.33.2331
Hanessian, 2005, Synthetic Studies in the Intramolecular Carbocyclization of N-Acyloxyiminium Ions. Stereoelectronic and Steric Implications of Nucleophilic Alkene, Alkyne, and Allene Tethers, Org. Chem., 70, 5070, 10.1021/jo050326w
Inui, 2001, Control of C-C and C–N Bond Cleavage of 2H-Azirine by Means of the Excitation Wavelength: Studies in Matrices and in Solutions, Chem. Commun., 2001, 1036, 10.1039/b102384p
Iravani, 2003, Trimerization of Phenylacetonitrile. InMe3 as a Base for C-H Acidic Nitriles, Organometallics, 22, 4129, 10.1021/om0303956
Jochims, 1970, Ketenimines. Geometry and barriers to racemization, J. Am. Chem. Soc, 92, 5524, 10.1021/ja00721a044
Jalli, 2015, One-pot four component synthesis of novel 3-furyl coumarin derivatives, J. Chem. Sci., 128, 217, 10.1007/s12039-015-1014-8
Jin, 2015, Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines, J. Org. Chem., 80, 6062, 10.1021/acs.joc.5b00466
Kirsch, 2004
Krow, 1971, Synthesis and Reactions of Ketenimines, Angew. Chem. Ed, 10, 435, 10.1002/anie.197104351
Kim, 2011, Sulfonyl and Phosphoryl Azides: Going Further Beyond the Click Realm of Alkyl and Aryl Azides, Chem. Asian. J., 6, 2618, 10.1002/asia.201100340
Kaneti, 1982, Theoretical study of ketenimine: Geometry, electronic properties, force constants and barriers to inversion and rotation, J. Mol. Struct., 87, 205, 10.1016/0166-1280(82)80054-7
Kaufman, 1970, Reaction of ethyl azidoformate with dimethyl- and diethylketen-N-(p-tolyl) imine, J. Org. Chem., 35, 4244, 10.1021/jo00837a011
Katagiri, 2009, Preparations and reactions of 2-trifluoromethylketenimines, J. Fluor. Chem, 130, 714, 10.1016/j.jfluchem.2009.05.020
Khlebnikov, 2003, Cascade Transformations of (2,2-Diaryl-3,3-dichloroaziridin-1-yl) acetates, Russ. J. Org. Chem, 39, 559, 10.1023/A:1026068020111
Lu, 2012, The thriving chemistry of ketenimines. Chem. Soc. Rev. 41,5687–5705, Chem. Soc. Rev., 41, 5687, 10.1039/c2cs35159e
Laouiti, 2014, Exploring the Anionic Reactivity of Ynimines, Useful Precursors of Metalated Ketenimines, Org. Lett., 16, 2252, 10.1021/ol500749h
Long, 2013, Efficient Aldol-Type Reaction of O-Protected α-Hydroxy Aldehydes and N-Trimethylsilyl Ketene Imines: Synthesis of β, γ-Dihydroxy-Nitriles, Eur. J. Org. Chem, 2013, 5127, 10.1002/ejoc.201300430
Moss, 1995, Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995), Pure. Appl. Chem., 67, 1307, 10.1351/pac199567081307
Molina, 1991, Domino reactions. One-pot preparation of fluoreno[2,3,4-ij] isoquinoline derivatives from conjugated ketene imines, J. Org. Chem., 56, 4008, 10.1021/jo00012a039
Marchand-Brynaert, 1972, Cycloadditions of keteneimmonium cations to olefins and dienes. New synthesis of four-membered rings, J. Am. Chem. Soc., 94, 2870, 10.1021/ja00763a062
Maity, 2018, Carbene Formation and Transfer at a Dinickel Active Site, J. Organomet. Chem., 37, 2437, 10.1021/acs.organomet.8b00261
Nicolaou, 1996
Nicolaou, 2003
Nicolaou, 2000, The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century, Angew. Chem. Int. Ed., 39, 44, 10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L
Orru, 2003, Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds, Synth., 10, 1471, 10.1055/s-2003-40507
Osisioma, 2018, Wavelength-dependent photochemistry of 2-azidovinylbenzene and 2-phenyl-2H-azirine, J. Mol. Struct., 1172, 94, 10.1016/j.molstruc.2018.04.042
Peng, 2015, C-terminal peptide extension via gas-phase ion/ion reactions, Int. J. Mass Spectrom., 391, 17, 10.1016/j.ijms.2015.07.027
Pujol, 2017, A Nucleophilic Gold (III) Carbene Complex, Angew. Chem. Int. Ed., 56, 12264, 10.1002/anie.201706197
Qian, 2016, Palladium-Catalyzed Migratory Insertion of Isocyanides for Synthesis of C-Phosphonoketenimines, ACS Catal, 6, 4715, 10.1021/acscatal.6b01253
Qiu, 2016, Ketenimines from Isocyanides and Allyl Carbonates: PalladiumCatalyzed Synthesis of β, γ-Unsaturated Amides and Tetrazoles, Angew. Chem., 128, 15603, 10.1002/ange.201609034
Rautenstrauch, 1984, 2-Cyclopentenones from 1-ethynyl-2-propenyl acetates Org, Chem., 49, 950
Simon, 1968, Stereochemistry of carbodiimides and ketenimines, Rev. Roum. Chim., 13, 381
Staudinger, 1919, Uber neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine, Helv. Chim. Acta., 2, 635, 10.1002/hlca.19190020164
Stevens, 1953, Nitrogen Analogs of Ketenes. A New Method of Preparation, J. Am. Chem. Soc., 75, 657, 10.1021/ja01099a043
Stevens, 1958, Nitrogen Analogs of Ketenes. V. Formation of the Peptide Bond, J. Am. Chem. Soc., 80, 4065, 10.1021/ja01548a059
Stevens, 1964, Nitrogen Analogs of Ketenes. VI.1 Dehydration of Amides, Org. Chem., 29, 34, 10.1021/jo01024a007
Shi, 2005, Synthesis of 2-Cyclopentenones by Gold(I)-Catalyzed Rautenstrauch Rearrangement, J. Am. Chem. Soc., 127, 5802, 10.1021/ja051689g
Sosa, 2008, Synthesis of Alkynyl Ethers and Low-Temperature Sigmatropic Rearrangement of Allyl and Benzyl Alkynyl Ethers, Org. Lett., 10, 5091, 10.1021/ol802147h
Tlili, 2013, Formation of C-SCF3 Bonds through Direct TrifluoromethylthiolationAngew, Chem. Int., 52, 6818, 10.1002/anie.201301438
Toulgoat, 2014, Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept, Eur. J. Org. Chem., 2014, 2415, 10.1002/ejoc.201301857
Weragoda, 2017, Singlet Photoreactivity of 3-Methyl-2-phenyl-2H-azirine, J. Chem., 70, 413
Wolf, 1996, Novel Heterocumulenes: Bisiminopropadienes and Linear Ketenimines, Chem. Eur. J., 2, 1318, 10.1002/chem.19960021020
Woodward, 1961, A NEW SYNTHESIS OF PEPTIDES, Am. Chem. Soc., 4, 1007, 10.1021/ja01465a069
Wu, 2017, Trifluoroacetic Anhydride-Promoted Copper(I)-Catalyzed Interrupted Click Reaction: From 1,2,3-Triazoles to 3- Trifluoromethyl-Substituted 1,2,4-Triazinones, Angew. Chem Int., 56, 10476, 10.1002/anie.201705620
Wang, 2013, J. Org. Chem., 78, 6233, 10.1021/jo400960e
Xiong, 2021, One-Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)-Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts, Chin. Chem. Lett., 39, 1553, 10.1002/cjoc.202000639
Yoo, 2009, Copper-Catalyzed Multicomponent Reactions: Securing a Catalytic Route to Ketenimine Intermediates and their Reactivities, Curr. Org. Chem., 13, 1766, 10.2174/138527209789630497
Yoo, 2007, Copper-Catalyzed Synthesis of N-Sulfonyl-1,2,3-triazoles: Controlling SelectivityAngew, Chem. Int., 46, 1730, 10.1002/anie.200604241
Yavari, 2012, One-pot synthesis of 2,6-diamino-4-sulfonamidopyrimidines from sulfonyl azides, terminal alkynes and cyanoguanidine, Tetrahedron Lett., 53, 942, 10.1016/j.tetlet.2011.12.041
Yavari, 2012, Copper-catalyzed one-pot synthesis of tetrasubstituted pyrazoles from sulfonyl azides, terminal alkynes, and hydrazonoyl chloride, Tetrahedron Lett., 53, 1889, 10.1016/j.tetlet.2012.01.083
Yu, 2014, Synthesis of α, β-unsaturated amides and iminocoumarins from N, N-disulfonyl ynamides with aldehydes via the ketenimine intermediate, Org Biomol. Chem., 12, 3986, 10.1039/c4ob00513a
Zhu, J., Bienaymé, H., 2005. Multicomponent Reactions. France: Eds. Wiley: Weinheim.
Zhang, 2019, The Generation of Difluoroketenimine and Its Application in the Synthesis of α, α-Difluoro-β-amino Amides, Angew. Chem., 131, 5800, 10.1002/ange.201901591
Zhang, 2014, Comparison of the Photochemistry of 3–Methyl-2-phenyl–2H–azirine and 2–Methyl-3-phenyl–2H–azirine, J. Org. Chem., 79, 653, 10.1021/jo402443w
Zhang, 2009, Synthesis of Amidines Using N-Allyl Ynamides. A Palladium-Catalyzed Allyl Transfer through an Ynamido-π-Allyl Complex, Org. Lett., 11, 899, 10.1021/ol802844z