Recent advances in synthesis of ketenimines

Arabian Journal of Chemistry - Tập 15 - Trang 104098 - 2022
Mohammad Bayat1, Davood Gheidari2, Morteza Mehrdad2
1Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran
2Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran

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