Schiff Bases: A Short Survey on an Evergreen Chemistry Tool

The review reports a short biography of the Italian naturalized chemist Hugo Schiff and an outline on the synthesis and use of his most popular discovery: the imines, very well known and popular as Schiff Bases. Recent developments on their “metallo-imines” variants have been described. The applications of Schiff bases in organic synthesis as partner in Staudinger and hetero Diels-Alder reactions, as “privileged” ligands in the organometallic complexes and as biological active Schiff intermediates/targets have been reported as well.

[1]  M. P. Cohen Clinical, pathophysiological and structure/function consequences of modification of albumin by Amadori-glucose adducts. , 2013, Biochimica et biophysica acta.

[2]  M. Xie,et al.  Cu(I)/TEMPO-Catalyzed Aerobic Oxidative Synthesis of Imines Directly from Primary and Secondary Amines under Ambient and Neat Conditions. , 2013 .

[3]  S. Peng,et al.  Preparation of Imines by Oxidative Coupling of Benzyl Alcohols with Amines Catalysed by Dicopper Complexes , 2013 .

[4]  M. Largeron Protocols for the Catalytic Oxidation of Primary Amines to Imines , 2013 .

[5]  J. Joseph,et al.  Quinoxaline-based Schiff base transition metal complexes: review , 2013 .

[6]  Adam Noble,et al.  Nitro-Mannich reaction. , 2013, Chemical reviews.

[7]  Peter D. Frischmann,et al.  Metallocavitands: an emerging class of functional multimetallic host molecules. , 2013, Chemical Society reviews.

[8]  M. Benohoud,et al.  Catalytic enantioselective [4 + 2]-cycloaddition: a strategy to access aza-hexacycles. , 2013, Chemical Society reviews.

[9]  H. Miyamura,et al.  Selective imine formation from alcohols and amines catalyzed by polymer incarcerated gold/palladium alloy nanoparticles with molecular oxygen as an oxidant. , 2013, Chemical communications.

[10]  S. Matsunaga,et al.  Multimetallic Schiff Base Complexes as Cooperative Asymmetric Catalysts , 2013 .

[11]  M. Largeron,et al.  Bioinspired Oxidation Catalysts , 2013, Science.

[12]  H. Miyamura,et al.  Discovery of a metalloenzyme-like cooperative catalytic system of metal nanoclusters and catechol derivatives for the aerobic oxidation of amines. , 2012, Journal of the American Chemical Society.

[13]  Xiao-yi Wen,et al.  Design, synthesis and antitumor activities of fluoroquinolone C-3 heterocycles (IV): s-triazole Schiff–Mannich bases derived from ofloxacin , 2012 .

[14]  A. Salem,et al.  Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M(II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2) , 2012 .

[15]  A. D. Allen,et al.  New Directions in Ketene Chemistry: The Land of Opportunity , 2012 .

[16]  Arjan W. Kleij,et al.  Recent advances with π-conjugated salen systems. , 2012, Chemical Society reviews.

[17]  Zhangjing Zhang,et al.  Functional mixed metal-organic frameworks with metalloligands. , 2011, Angewandte Chemie.

[18]  E. Bandini,et al.  Hetero‐Diels–Alder (HDA) Strategy for the Preparation of 6‐Aryl‐ and Heteroaryl‐Substituted Piperidin‐2‐one Scaffolds: Experimental and Theoretical Studies , 2011 .

[19]  Lan Jiang,et al.  Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions. , 2011, Chemical communications.

[20]  Yasuhiro Shiraishi,et al.  One-pot synthesis of imines from alcohols and amines with TiO2 loading Pt nanoparticles under UV irradiation. , 2011, Chemical communications.

[21]  Sho-ichi Yamagishi,et al.  Role of advanced glycation end products (AGEs) and receptor for AGEs (RAGE) in vascular damage in diabetes , 2011, Experimental Gerontology.

[22]  J. Fossey,et al.  Catalytic enantioselective formation of C-C bonds by addition to imines and hydrazones: a ten-year update. , 2011, Chemical reviews.

[23]  A. Szumna Inherently chiral concave molecules--from synthesis to applications. , 2010, Chemical Society reviews.

[24]  D. Gutsulyak,et al.  Chemoselective catalytic hydrosilylation of nitriles. , 2010, Angewandte Chemie.

[25]  M. Benaglia,et al.  Trichlorosilane‐Mediated Stereoselective Reduction of C=N Bonds , 2010 .

[26]  A. Dalla Cort,et al.  Metal-salophen-based receptors for anions. , 2010, Chemical Society reviews.

[27]  C. R. Prakash,et al.  Synthesis and anti-microbial screening of novel schiff bases of 3-amino-2-methyl quinazolin 4-(3H)-one , 2010, Journal of advanced pharmaceutical technology & research.

[28]  Nenad Vuković,et al.  Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: synthesis and in vitro assessments. , 2010 .

[29]  Arjan W. Kleij,et al.  Cooperative multimetallic catalysis using metallosalens. , 2010, Chemical communications.

[30]  D. Milstein,et al.  Direct synthesis of imines from alcohols and amines with liberation of H2. , 2010, Angewandte Chemie.

[31]  E. Bandini,et al.  A straightforward synthesis of conhydrine by hetero Diels–Alder strategy mediated by microwaves , 2010 .

[32]  R. Batey,et al.  Lewis Acid catalyzed three-component hetero-Diels-alder (povarov) reaction of N-arylimines with strained norbornene-derived dienophiles. , 2010, The Journal of organic chemistry.

[33]  S. Ueno,et al.  [4+2] cycloaddition of o-xylylenes with imines using palladium catalyst. , 2009, Journal of the American Chemical Society.

[34]  E. Jnoff,et al.  Multicomponent reactions for the synthesis of complex piperidine scaffolds. , 2009, Angewandte Chemie.

[35]  V. Kouznetsov Recent Synthetic Developments in a Powerful Imino Diels—Alder Reaction (Povarov Reaction): Application to the Synthesis of N‐Polyheterocycles and Related Alkaloids. , 2009 .

[36]  D. N. Dhar,et al.  Applications of metal complexes of Schiff bases-A review , 2009 .

[37]  N. de Kimpe,et al.  Highly stereoselective synthesis of beta-lactams utilizing alpha-chloroimines as new and powerful chiral inductors. , 2008, Chemistry.

[38]  K. Gupta,et al.  Catalytic activities of Schiff base transition metal complexes , 2008 .

[39]  C. Valdés,et al.  Multicomponent and One‐Pot Synthesis of Trisubstituted Pyridines Through a Pd‐Catalyzed Cross‐Coupling/Cross‐Coupling/Cycloaddition Sequence. , 2008 .

[40]  X. Mu,et al.  Synthesis of Venlafaxine from Azadiene via a Hetero-Diels-Alder Approach: New Microwave-Assisted Transketalization and Hydroxymethylation Reactions , 2008 .

[41]  M. Grillo,et al.  Advanced glycation end-products (AGEs): involvement in aging and in neurodegenerative diseases , 2008, Amino Acids.

[42]  T. T. Tidwell Hugo (Ugo) Schiff, Schiff Bases, and a Century of β‐Lactam Synthesis , 2008 .

[43]  E. De Clercq,et al.  Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. , 2007, Molecules.

[44]  Pengcheng Li,et al.  Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. , 2007, Carbohydrate research.

[45]  M. Gopalakrishnan,et al.  New environmentally-friendly solvent-free synthesis of imines using calcium oxide under microwave irradiation , 2007 .

[46]  H. Ge,et al.  Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. , 2007, European journal of medicinal chemistry.

[47]  R. H. Holm,et al.  Metal Complexes of Schiff Bases and β‐Ketoamines , 2007 .

[48]  H. A. Stefani,et al.  Eco-friendly synthesis of imines by ultrasound irradiation , 2007 .

[49]  H. Naeimi,et al.  Mild and convenient one pot synthesis of Schiff bases in the presence of P2O5/Al2O3 as new catalyst under solvent-free conditions , 2006 .

[50]  Mari Sithambaram Karthikeyan,et al.  Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety. , 2006, Bioorganic & medicinal chemistry.

[51]  A. Procopio,et al.  Erbium(III) Triflate: A Valuable Catalyst for the Synthesis of Aldimines, Ketimines, and Enaminones. , 2006 .

[52]  P. Yogeeswari,et al.  Abacavir prodrugs: microwave-assisted synthesis and their evaluation of anti-HIV activities. , 2006, Bioorganic & medicinal chemistry letters.

[53]  A. Bongini,et al.  A Hetero Diels–Alder Concerted vs. Aldol Stepwise Mechanism in the Cyclization of Silyloxyazadienes with Aldehydes: A Theoretical Study , 2006 .

[54]  Paola Vicennati,et al.  From 3‐Trialkylsilyloxy‐2‐aza‐1,3‐dienes to Biological Interesting Molecules Through Cyclization Reactions , 2005 .

[55]  F. Verpoort,et al.  Synthesis of Schiff Base-Ruthenium Complexes and Their Applications in Catalytic Processes , 2005 .

[56]  Mehmet Tümer,et al.  Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity , 2005 .

[57]  V. C. Soares,et al.  Molecular Sieves in Ionic Liquids as an Efficient and Recyclable Medium for the Synthesis of Imines. , 2005 .

[58]  S. Sridhar,et al.  Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents. , 2005, European journal of medicinal chemistry.

[59]  A. Chakraborti,et al.  Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones , 2004 .

[60]  P. A. Vigato,et al.  The challenge of cyclic and acyclic schiff bases and related derivatives , 2004 .

[61]  T. Katsuki,et al.  Unique asymmetric catalysis of cis-beta metal complexes of salen and its related Schiff-base ligands. , 2004, Chemical Society reviews.

[62]  P. Cozzi Metal-Salen Schiff base complexes in catalysis: practical aspects. , 2004, Chemical Society reviews.

[63]  J. Aizpurua,et al.  Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products , 2004 .

[64]  C. Valdés,et al.  N‐Trialkylsilylimines as Coupling Partners for Pd‐Catalyzed C—N Bond‐Forming Reactions: One‐Step Synthesis of Imines and Azadienes from Aryl and Alkenyl Bromides. , 2004 .

[65]  S. Christensen,et al.  Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. , 2004, Journal of natural products.

[66]  Yo-Sep Min,et al.  A study on the development of CVD precursors V – syntheses and characterization of new N-alkoxy-β-ketoiminate complexes of titanium , 2004 .

[67]  C. Valdés,et al.  N-trialkylsilylimines as coupling partners for pd-catalyzed C[bond]N-forming reactions: one-step synthesis of imines and azadienes from aryl and alkenyl bromides. , 2004, Angewandte Chemie.

[68]  J. Tamariz,et al.  Infrared Irradiation: Effective Promoter in the Formation of N‐Benzylideneanilines in the Absence of Solvent , 2004 .

[69]  Wim J. N. Meester,et al.  Intramolecular Staudinger ligation: a powerful ring-closure method to form medium-sized lactams. , 2003, Angewandte Chemie.

[70]  E. Jacobsen,et al.  Privileged Chiral Catalysts , 2003, Science.

[71]  Jørgensen,et al.  Catalytic Asymmetric Hetero-Diels-Alder Reactions of Carbonyl Compounds and Imines. , 2000, Angewandte Chemie.

[72]  E. Jacobsen,et al.  Asymmetric catalysis of epoxide ring-opening reactions. , 2000, Accounts of chemical research.

[73]  U. Möllmann,et al.  Semisynthetic derivatives of madurahydroxylactone and their antibacterial activities. , 1999, The Journal of antibiotics.

[74]  J. Barluenga,et al.  Chiral Heterosubstituted 1,3-Butadienes: Synthesis and [4 + 2] Cycloaddition Reactions , 1999 .

[75]  D. Sriram,et al.  Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. , 1999, Farmaco.

[76]  R. Varma,et al.  Solvent-free synthesis of N-sulfonylimines using microwave irradiation , 1999 .

[77]  E. Jnoff,et al.  Asymmetric Diels-Alder reactions of 2-azadienes catalyzed by a chiral copper(II) complex. A general route to enantiomerically pure piperidones , 1999 .

[78]  J. Ellman,et al.  Synthesis of Enantiomerically Pure N-tert-Butanesulfinyl Imines (tert-Butanesulfinimines) by the Direct Condensation of tert-Butanesulfinamide with Aldehydes and Ketones , 1999 .

[79]  P. Zarantonello,et al.  Synthesis and Use of N-(Trimethylsilyl)imines , 1998 .

[80]  R. Varma,et al.  Clay catalyzed synthesis of imines and enamines under solvent-free conditions using microwave irradiation , 1997 .

[81]  G. Robertson Imines and Their N‐Substituted Derivatives: NH, NR and N‐Haloimines , 1996 .

[82]  M. Gallop,et al.  Trimethylorthoformate: A mild and effective dehydrating reagent for solution and solid phase imine formation , 1995 .

[83]  Jianhua Ren,et al.  Synthesis of Sterically Hindered Imines. , 1994 .

[84]  Ye Zhenhuan,et al.  Synthesis, characterization and antifungal activity of glycylglycine Schiff base complexes of 3d transition metal ions , 1993 .

[85]  E. Mezzina,et al.  Preparation of 1,2 aminols from cyanohydrins viaN-diisobutylaluminium imines. , 1993 .

[86]  L. I. Lavrinovich,et al.  Synthesis of functional derivatives of 2-methylenecyclopentane and 2-methylenecyclohexane based on the allylborylation of imines, nitriles, isocyanates, and isothiocyanates by cycloalkenylmethyl(dipropyl)boranes , 1992 .

[87]  E. Mezzina,et al.  N-Metalloimines: A New Approach to a-Amino Alcohols from Aldehydes. , 1992 .

[88]  E. Mezzina,et al.  N-metallo imines: A new approach to α-amino alcohols from aldehydes. , 1991 .

[89]  M. Lai,et al.  Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus. , 1990, Journal of medicinal chemistry.

[90]  E. Bandini,et al.  Metallo-imines: Useful reagents in organic synthesis , 1990 .

[91]  M. J. Nugent,et al.  Silicon-assisted synthesis of β-lactams , 1988 .

[92]  D. Giacomini,et al.  A synthetic approach to azetidinones from nitriles and lithiumtriethoxyaluminium hydride. , 1986 .

[93]  C. Kaiser,et al.  Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake , 1985 .

[94]  D. Hart,et al.  Preparation of primary amines and 2-azetidinones via N-(trimethylsilyl)imines , 1983 .

[95]  A. Kunicki,et al.  The reactions of tetraalkylaluminoxanes with benzonitrile , 1980 .

[96]  W. Foye,et al.  Comprehensive organic chemistry , 1980 .

[97]  F. Westheimer,et al.  Catalysis by molecular sieves in the preparation of ketimines and enamines , 1971 .

[98]  H. Hoberg,et al.  ADDITION VON AL‐N(AMIN)‐VERBINDUNGEN AN BENZONITRIL , 1970 .

[99]  T. Hirabayashi,et al.  Insertion reactions of diethylaluminium derivatives II. reaction of diethylaluminium dimethylamide and diethylaluminium ethanethiolate with nitriles , 1970 .

[100]  H. Hoberg,et al.  Das verhalten von dialkyl-aluminium-amiden gegenüber benzonitril , 1969 .

[101]  A. Meller,et al.  Monomere und dimere hochhalogenierte Iminoborane , 1968 .

[102]  L. Chan,et al.  Syntheses and ultraviolet spectra of N-organosilyl ketimines , 1967 .

[103]  A. Weissberger Methoden der Organischen Chemie (Houben-Weyl). , 1964, Science.

[104]  R. Layer The Chemistry of Imines. , 1963 .

[105]  C. Krüger,et al.  Über die Einwirkung von Natrium-bis-trimethylsilyl-amid auf Benzophenon, Benzaldehyd und Benzochinon , 1963 .

[106]  P. L. Pickard,et al.  An Improved Method of Ketimine Synthesis , 1961 .

[107]  W. Jenkins,et al.  The mechanism of the transamination reaction. , 1959, Journal of cellular and comparative physiology.

[108]  A. MacDiarmid,et al.  The Preparation of Di-n-butylboron Cyanide by the Interaction of Di-n-butylboron Chloride with Trimethylsilyl Cyanide1 , 1959 .

[109]  J. Billman,et al.  Reduction of Schiff Bases. II. Benzhydrylamines and Structurally Related Compounds1a,b , 1958 .

[110]  H. Mosher,et al.  Notes - Reduction of o-Bromoanisole by Lithium Dineopentylamide , 1957 .

[111]  J. H. Boyer,et al.  Alkyl and Aryl Azides. , 1954 .

[112]  R. Shriner The Systematic Identification of Organic Compounds: , 1936, Nature.

[113]  W. Fischer,et al.  Über die Kernkondensation von Phenolen und Phenoläthern mit Nitrilen zu Phenol- und Phenoläther-ketimiden und -ketonen. IV.: Synthesen mit Phenol, o- und m-Kresol, p-Kresol-methyläther und p-Kresol , 1929 .

[114]  G. Reddelien Über die Zersetzung von Anilen. (Über die katalytische Wirkungsweise von Halogenwasserstoffsäuren bei Kondensationen, II) , 1920 .

[115]  G. Reddelien ber Selbstkondensation bei Anilen. (Studien ber Zinkchlorid als Kondensationsmittel III) , 1913 .

[116]  E. Ott Über symmetrische und asymmetrische Dicarbonsäure-chloride II , 1913 .

[117]  K. Langheld Über das Verhalten von α‐Aminosäuren gegen Natriumhypochlorit , 1909 .

[118]  L. Claisen Ueber eine eigenthümliche Umlagerung , 1896 .

[119]  Paul Knochel,et al.  Comprehensive organic synthesis , 2014 .

[120]  B. Krammer,et al.  Antibacterial effect of some benzopyrone derivatives. , 2010, European journal of medicinal chemistry.

[121]  M. Noolvi,et al.  Synthesis and antimicrobial activity of 7-(2-substituted phenylthiazolidinyl)-benzopyran-2-one derivatives. , 2010, European journal of medicinal chemistry.

[122]  B. Brzeziński,et al.  Biological Properties of Schiff Bases and Azo Derivatives of Phenols , 2009 .

[123]  F. Rutjes,et al.  Organocatalysed asymmetric Mannich reactions. , 2008, Chemical Society reviews.

[124]  A. Mishra,et al.  Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. , 2008, European journal of medicinal chemistry.

[125]  A. Marsaioli,et al.  Antimycobacterial and cytotoxicity activity of synthetic and natural compounds , 2007 .

[126]  K. R. Desai,et al.  SYNTHESIS OF SOME SCHIFF BASES,THIAZOLIDINONES AND AZETIDINONES DERIVED FROM 2,6-DIAMINOBENZO[1,2-d:4,5-d'] BISTHIAZOLE AND THEIR ANTICANCER ACTIVITIES , 2001 .

[127]  Koichi Tanaka,et al.  Clean and efficient condensation reactions of aldehydes and amines in a water suspension medium , 2000 .

[128]  G. Kaupp,et al.  Quantitative solid–solid synthesis of azomethines , 1998 .

[129]  F. Delmas,et al.  Synthesis of novel functionalized 5-nitroisoquinolines and evaluation of in vitro antimalarial activity , 1995 .

[130]  E. Bandini,et al.  β-Lactams from Ester Enolates and Metalloimines: Synthesis and Reactivity of tert-Butyldimethylsilylimines , 1991 .

[131]  J. Guillemin,et al.  A convenient synthesis of enolizable N-trialkylsilylimines using vacuum gas-solid reactions , 1988 .

[132]  D. Giacomini,et al.  Reaction of silylimines with ester enolates. Synthesis of N-unsubstituted azetidinones starting from nitriles , 1988 .

[133]  D. Boger,et al.  Hetero Diels-Alder methodology in organic synthesis , 1987 .

[134]  D. Giacomini,et al.  β-Lactams from esters and silylimines: a revaluation. Synthesis of N-unsubstituted 4-alkyl-β-lactams , 1987 .

[135]  W. Ollis,et al.  Comprehensive organic chemistry : the synthesis and reactions of organic compounds , 1978 .

[136]  H. Hoberg,et al.  Addition der Cα-H-Bindung von N-Aluminium-iminen und Iminen an Nitrile , 1970 .

[137]  S. Patai The chemistry of the carbon-nitrogen double bond , 1970 .

[138]  H. Hoberg,et al.  Addition von AlNamin‐Verbindungen an Benzonitril , 1970 .

[139]  H. Weingarten,et al.  A versatile new enamine synthesis , 1967 .

[140]  C. Young,et al.  Ketimines. III. ι-Cyclohexylalkyl Alkyl Type1 , 1951 .

[141]  K. Hoesch,et al.  Eine neue Synthese aromatischer Ketone. II. Künstliche Darstellung des Maclurins und ihm verwandter Ketone , 1917 .

[142]  K. Hoesch Eine neue Synthese aromatischer Ketone. I. Darstellung einiger Phenol‐ketone , 1915 .

[143]  Istituto tecnico di Palermo.,et al.  Giornale di Scienze Naturali ed Economiche , 1871 .

[144]  Hugo Schiff,et al.  Eine neue Reihe organischer Diamine , 1866 .

[145]  H. Schiff Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen , 1864 .

[146]  H. Schiff Ueber die Einwirkung des Phosphorsuperchlorids auf einige anorganische Säuren , 1857 .