Recent developments on the chemistry of aliphatic nitro compounds under aqueous medium

Aliphatic nitro derivatives represent an important class of useful molecules in organic synthesis. The versatility of these compounds is largely due to their easy availability and transformation into a variety of diverse functionalities. Moreover, aliphatic nitro compounds are very important building blocks (both as nucleophiles or as electrophiles) for the generation of new carbon–carbon bonds, mainly via nitroaldol-Henry reactions, Michael reactions and Diels–Alder cycloadditions. Usually, organic solvents are believed to be necessary for achieving the best efficiency in the reactions of aliphatic nitro compounds and, only recently, it has been shown that these reactions are also very efficient using water as reaction medium. Such progress in the chemistry of aliphatic nitro compounds is particularly attractive to industry since the replacement of toxic solvents still remains a crucial (and expensive) challenge. Thus, this report is focused on the chemistry of aliphatic nitro derivatives performed in aqueous media.

[1]  R. A. Ellison Methods for the Synthesis of 3-Oxocyclopentenes , 1973 .

[2]  MiyashitaMasaaki,et al.  NEW SYNTHESIS OF γ-KETO ACIDS FROM NITROOLEFINS AND CARBOXYLIC ACID DIANIONS , 1982 .

[3]  H. Hosni,et al.  N-Unsubstituted (Carbamoyloxy)nitrostyrenes: A New Series of Aryl-β-nitroalkenes with Fungicidal Properties , 1987 .

[4]  L. Vaccaro,et al.  Thiolysis of Alkyl‐ and Aryl‐1,2‐epoxides in Water Catalyzed by InCl3 , 2002 .

[5]  R. Ballini Recent Progress on the Ring Cleavage of Cyclic 2-Nitro Ketones by External Nucleophiles , 1999 .

[6]  L. Vaccaro,et al.  Lewis-acid catalyzed organic reactions in water. The case of AlCl(3), TiCl(4), and SnCl(4) believed to be unusable in aqueous medium. , 2001, The Journal of organic chemistry.

[7]  A. Palmieri,et al.  Acyclic α-nitro ketones : a versatile class of α-functionalized ketones in organic synthesis , 2005 .

[8]  D. Seebach,et al.  Diastereoselective Synthesis of Nitroaldol Derivatives , 1982 .

[9]  R. Ballini,et al.  RECENT PROGRESS IN THE SYNTHESIS AND REACTIVITY OF NITROKETONES. A REVIEW , 1990 .

[10]  F. Fringuelli,et al.  Uncatalyzed [4 + 2] cycloadditions of 3-nitrocoumarins with vinyl ethers in solventless conditions. A new entry to chromene derivatives. , 2002, The Journal of organic chemistry.

[11]  L. Vaccaro,et al.  Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides , 2001 .

[12]  F. Tanaka,et al.  Organocatalytic direct michael reaction of ketones and aldehydes with beta-nitrostyrene in brine. , 2006, Journal of the American Chemical Society.

[13]  A. Saikia,et al.  An Improved Synthesis of Conjugated Nitroolefins , 1994 .

[14]  Y. Tohda,et al.  Nucleophilic Reaction upon Electron-Deficient Pyridone Derivatives. XII. Novel Additions of 3,5-Dinitro-2-pyridone with Ethyl Vinyl Ether: Formation and Reactions of a Six-membered Cyclic Nitronate , 1993 .

[15]  D. Ager,et al.  1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. , 1996, Chemical reviews.

[16]  R. Ballini,et al.  Nitroaldol Reaction in Aqueous Media: An Important Improvement of the Henry Reaction. , 1997, The Journal of organic chemistry.

[17]  Ronald Breslow,et al.  Hydrophobic acceleration of Diels-Alder reactions , 1980 .

[18]  R. Ballini,et al.  One-Pot Diastereoselective Synthesis of 2-Acyl-4-nitrocyclohexanol Derivatives in Aqueous Medium , 2000 .

[19]  L. Vaccaro,et al.  Epoxidation of α,β-unsaturated ketones in water. An environmentally benign protocol , 2003 .

[20]  Luigi Vaccaro,et al.  TBAF-catalyzed [3 + 2]cycloaddition of TMSN3 to 3-nitrocoumarins under SFC: an effective green route to chromeno[3,4-d][1,2,3]triazol-4(3H)-ones , 2005 .

[21]  F. Felluga,et al.  Highly diastereoselective synthesis of cyclic nitronic esters from 1-(4-morpholinyl)-1-phenylpropene with nitroolefins , 1989 .

[22]  André Lubineau,et al.  Water-promoted organic reactions. Michael addition of nitroalkanes to methylvinylketone under neutral conditions , 1992 .

[23]  O. Piermatti,et al.  [4 + 2] cycloadditions of nitroalkenes in water. Highly asymmetric synthesis of functionalized nitronates. , 2001, The Journal of organic chemistry.

[24]  L. Vaccaro,et al.  Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions. , 2003, The Journal of organic chemistry.

[25]  Hee-doo Kim,et al.  A practical preparations of conjugated nitroalkenes , 1986 .

[26]  F. Gasparrini,et al.  Enantiomerization study of some α-nitroketones by dynamic high-resolution gas chromatography , 2003 .

[27]  S. Denmark,et al.  Synthesis of (-)-7-epiaustraline and (-)-1-epicastanospermine. , 2000, The Journal of organic chemistry.

[28]  A. Palmieri,et al.  Cetyltrimethylammonium hydroxide (CTAOH) as a general, ecofriendly catalyst for the formation of carbon–carbon bond through nitroalkanes , 2004 .

[29]  L. Vaccaro,et al.  Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0 , 2001 .

[30]  F. Sztaricskai,et al.  2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones , 1997 .

[31]  R. Ballini,et al.  Synthesis of ω-Nitro Acids and ω-Amino Acids by Ring Cleavage of α-Nitrocycloalkanones , 1999 .

[32]  A. Fontana,et al.  Equilibrium Constants for Ionisation and Enolisation of 3‐Nitrobutan‐2‐one , 2000 .

[33]  F. A. Luzzio,et al.  The Henry reaction: recent examples , 2001 .

[34]  J. Betancourt,et al.  Activity of a nitroalkene derivative, 1-(5-bromofur-2-il)-2-bromo-2-nitroethene, in the Salmonella/microsome assay and the mouse bone marrow micronucleus test. , 1997, Mutation research.

[35]  C. W. Scaife,et al.  280. Aliphatic nitro-compounds. Part I. Preparation of nitro-olefins by dehydration of 2-nitro-alcohols , 1947 .

[36]  R. Cookson,et al.  A new synthesis of macrocyclic keto-lactones via ring expansion of 2-(3-hydroxypropyl)-2-nitrocycloalkanones , 1982 .

[37]  J. Plavec,et al.  [4 + 2] and [3 + 2] Cycloaddition reactions of 2',3'-dideoxy-3'-nitro-2',3'-didehydrothymidine with ethyl vinyl ether , 1993 .

[38]  A. Barrett,et al.  Conjugated Nitroalkenes: Versatile Intermediates in Organic Synthesis , 1986 .

[39]  M. Shipchandler The Utility of Nitroacetic Acid and its Esters in Organic Synthesis , 1979 .

[40]  T. Ho Synthesis of Jasmonoids, a Review , 1975 .

[41]  R. Woodward,et al.  The Reaction of Furan with Maleic Anhydride1 , 1948 .

[42]  C. Cheng,et al.  Synthesis of 5,7-dioxo-3-methyl-5,6,7,8-tetrahydropyrimido[5,4-e]-as-triazine. , 1968, Journal of medicinal chemistry.

[43]  L. Vaccaro,et al.  Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water , 2003 .

[44]  R. Ballini,et al.  Conjugated Addition Reactions of Nitroalkanes with Electrophilic Alkenes in Aqueous Media , 1998 .

[45]  O. Piermatti,et al.  Indium Salt-Promoted Organic Reactions , 2003 .

[46]  R. Ballini,et al.  Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) , 2004 .

[47]  S. Denmark,et al.  Tandem Cycloaddition Chemistry of Nitroalkenes: Probing the Remarkable Stereochemical Influence of the Lewis Acid. , 1999, The Journal of organic chemistry.

[48]  B. Carlson,et al.  Reaction of diazonium salts with dienes. Route to pyridazines and pyridazinium salts , 1975 .

[49]  N. Ono,et al.  Michael addition of secondary nitroalkanes to β-substituted α,β-unsaturated compounds , 1984 .

[50]  G. R. Lappin,et al.  THE SYNTHESIS OF -NITROSTYRENES , 1953 .

[51]  S. King,et al.  Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes , 1999 .

[52]  R. Ballini,et al.  A New, Simple, and General Synthesis of 1,3-, 1,4- and 1,5-Diketones from Functionalized Nitroalkanes , 1993 .

[53]  S. Denmark,et al.  Synthesis of (+)-1-epiaustraline. , 2001, The Journal of organic chemistry.

[54]  O. Piermatti,et al.  Water, a clean, inexpensive, and re-usable reaction medium. One-pot synthesis of (E)-2-aryl-1-cyano-1-nitroethenes , 2001 .

[55]  R. Ballini,et al.  Facile and Inexpensive Synthesis of 4-Oxoalkanoic Acids from Primary Nitroalkanes and Acrolein , 1986 .

[56]  R. Silverman,et al.  A Convenient Synthesis of 3-Alkyl-4-aminobutanoic Acids , 1989 .

[57]  P. Gramatica,et al.  Reaction of nitroolefins with raney nickel and sodium hypophosphite. A mild method for converting nitroolefins into ketones (or aldehydes). , 1983 .

[58]  J. Mcmurry,et al.  New method for the dehydration of nitro alcohols , 1975 .

[59]  O. Piermatti,et al.  Recent Advances in Lewis Acid Catalyzed Diels−Alder Reactions in Aqueous Media , 2001 .

[60]  Y. Tohda,et al.  Synthesis and a Novel Fragmentation of 6-Alkoxy-5,6-dihydro-4H-1,2-oxazine 2-Oxide , 1988 .

[61]  N. Ono,et al.  Anti-selective Michael addition of thiols and their analogs to nitro olefins , 1990 .

[62]  R. Ballini,et al.  The Michael reaction of nitroalkanes with conjugated enones in aqueous media , 1996 .

[63]  C. Avendaño,et al.  Unique Michael addition-initiated domino reaction for the stereoselective synthesis of functionalized macrolactones from alpha-nitroketones in water. , 2005, Organic letters.

[64]  Joel Jones,et al.  Organic reaction in water. Part 3¹: diastereoselectivity in Michael additions of thiophenol to nitro olefins in aqueous media , 2001 .

[65]  O. Piermatti,et al.  3-nitrocoumarins as dienophiles in the Diels-Alder reaction in water. An approach to the synthesis of nitrotetrahydrobenzo[c]chromenones and dihydrodibenzo[b,d]furans. , 2003, The Journal of organic chemistry.

[66]  M. S. Wadia,et al.  A Simple Unusual One-Step Conversion of Aromatic Aldehydes into Nitriles , 1985 .

[67]  R. Ballini,et al.  Functionalized Nitroalkanes as Useful Reagents for Alkyl Anion Synthons , 1989 .

[68]  R. Ballini,et al.  Chemoselective synthesis of functionalized conjugated nitroalkenes , 1992 .

[69]  O. Schales,et al.  Arylnitroalkenes: A New Group of Antibacterial Agents1 , 1952 .

[70]  L. Vaccaro,et al.  NaOH-Catalyzed Thiolysis of α,β-Epoxyketones in Water. A Key Step in the Synthesis of Target Molecules Starting from α,β-Unsaturated Ketones , 2004 .

[71]  D. Seebach,et al.  Dichloro[TADDOLato(2−)-O,O′]titanium/Dichlorobis[1-methylethoxy]titanium-Mediated, Highly Diastereo- and Enantioselective Additions of Silyl Enol Ethers to Nitro Olefins and [3+2] Cycloadditions of Primary Adducts to Acetylenes , 1999 .

[72]  K. Drexhage,et al.  Dyestuff Lasers and Light Collectors — Two New Fields of Application for Fluorescent Heterocyclic Compounds , 1984 .

[73]  R. Ballini,et al.  Nitroalkanes in aqueous medium as an efficient and eco-friendly source for the one-pot synthesis of 1,4-diketones, 1,4-diols, delta-nitroalkanols, and hydroxytetrahydrofurans. , 2003, The Journal of organic chemistry.

[74]  D. Seebach,et al.  2'-Nitro-2'-propen-1'-yl 2,2-dimethylpropanoate (NPP), a multiple coupling reagent , 1984 .

[75]  D. Rideout,et al.  Selective diels-alder reactions in aqueous solutions and suspensions , 1983 .

[76]  A. Palmieri,et al.  Conjugate additions of nitroalkanes to electron-poor alkenes: recent results. , 2005, Chemical reviews.

[77]  R. Ballini,et al.  Chemoselective Conversion of Conjugated Nitroalkenes into Ketones by Sodium Borohydride-Hydrogen Peroxide: A New Synthesis of 4-Oxoalkanoic Acids, Dihydrojasmone and (+)-exo-Brevicomin , 1994 .

[78]  O. Piermatti,et al.  Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols. , 1994 .

[79]  H. W. Scheeren,et al.  A simple entry towards novel bi- and tricyclic N-oxy-β-lactams by high pressure promoted tandem [4 + 2]/[3 + 2] cycloadditions of enol ethers and β-nitrostyrene , 1999 .

[80]  R. Ballini,et al.  A CONVENIENT SYNTHESIS OF 1-(2-FURYL)-2-NITROALK-1-ENES ON ALUMINA SURFACE WITHOUT SOLVENT , 1985 .

[81]  D. Bergbreiter,et al.  Michael additions of nitroalkanes to .alpha.,.beta.-unsaturated carbonyl compounds using potassium fluoride/basic alumina , 1987 .

[82]  D. Sinou Asymmetric Organometallic‐Catalyzed Reactions in Aqueous Media , 2002 .

[83]  Luigi Vaccaro,et al.  Ring Opening of Epoxides with Sodium Azide in Water. A Regioselective pH-Controlled Reaction , 1999 .

[84]  Luigi Vaccaro,et al.  InCl3-Catalyzed Regio- and Stereoselective Thiolysis of α,β-Epoxycarboxylic Acids in Water , 2005 .

[85]  D. Seebach,et al.  Dehydratisierung von Nitroaldolen mit Dicyclohexylcarbodiimid: Herstellung von Nitroolefinen unter milden Bedingungen , 1982 .

[86]  A. Palmieri,et al.  δ-Nitroalkanols as precursors for the one-pot synthesis of substituted tetrahydrofurans , 2003 .

[87]  Ulf M Lindström,et al.  Stereoselective organic reactions in water. , 2002, Chemical reviews.

[88]  L. Vaccaro,et al.  AlCl 3 as an efficient Lewis acid catalyst in water , 2001 .

[89]  K. Manabe,et al.  Green Lewis acid catalysis in organic synthesis , 2000 .

[90]  O. Piermatti,et al.  One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water , 2004 .

[91]  P. Wadgaonkar,et al.  Envirocat EPZGR as a New Heterogenous Catalyst for the Efficient Synthesis of Conjugated Nitroolefins , 1996 .

[92]  A. Linden,et al.  A Novel NO2/OH Exchange in ?-Nitro Ketones: A mechanistic investigation , 1998 .

[93]  G. Rousseau,et al.  New Method for the Reaction of Nitroalkanes with Unsaturated Esters , 1991 .

[94]  Chao-Jun Li,et al.  Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. , 2005, Chemical reviews.

[95]  A. Barrett Heterosubstituted nitroalkenes in synthesis , 1991 .

[96]  R. Varma,et al.  SYNTHESES AND SELECTED REDUCTIONS OF CONJUGATED NITROALKENES. A REVIEW , 1987 .

[97]  L. Vaccaro,et al.  First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines , 2003 .

[98]  O. Piermatti,et al.  SIMPLE AND EFFICIENT ONE-POT PREPARATION OF 3-SUBSTITUTED COUMARINS IN WATER , 1996 .

[99]  Ballini,et al.  Nitroalkanes as a new, convenient source of 1-acyl-2, 5-dialkylbenzene derivatives, in two steps , 2000, Journal of Organic Chemistry.

[100]  J. Y. Lee,et al.  Total synthesis of nonactin , 1995 .

[101]  G. Pollini,et al.  Tetramethylguanidine-Catalyzed Addition of Nitromethane to α,β-Unsaturated Carboxylic Acid Esters , 1972 .