Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 23
162
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide

, , , &
Pages 3400-3407 | Received 14 May 2014, Published online: 10 Oct 2014

REFERENCES

  • (a) Grison , C. ; Genève , S. ; Coutrot , P. Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams . Tetrahedron Lett. 2001 , 42 , 3831 – 3834 ; (b) Groaning , M. D. ; Meyers , A. I. Chiral nonracemic bicyclic lactams: Auxiliary-based asymmetric reactions . Tetrahedron 2000 , 56 , 9843 – 9873 ; (c) Dijkink , J. ; Cintrat , J.-C. ; Speckamp , W. N. ; Hiemstra , H. Enantioselective synthesis of a key tricyclic intermediate en route to (+)-gelsemine . Tetrahedron Lett. 1999 , 40 , 5919 – 5922 ; (d) Kuo , R.-Y. ; Chang , F.-R. ; Wu , Y.-C. A new propentdyopent derivative, rollipyrrole, from Rollinia mucosa Baill . Tetrahedron Lett. 2001 , 42 , 7907 – 7909 ; (e) Brower , J. O. ; Lightner , D. A. ; McDonagh , A. F. Aromatic congeners of bilirubin: Synthesis, stereochemistry, glucuronidation, and hepatic transport . Tetrahedron 2001 , 57 , 7813 – 7827 ; (f) Takabe , K. ; Suzuki , M. ; Nishi , T. ; Hiyoshi , M. ; Takamori , Y. ; Yoda , H. ; Mase , N. Convenient route to both enantiomers of chiral 5-hydroxypyrrolidin-2-one and 5-hydroxy-1,5-dihydropyrrol-2-one: reverse enantioselectivity in lipase-catalyzed kinetic resolution . Tetrahedron Lett. 2000 , 41 , 9859 – 9863 ; (g) Kobayashi , J. ; Sekiguchi , M. ; Shimamoto , S. ; Shigemori , H. ; Ohsaki , A. Echinophyllins C-F: New nitrogen-containing clerodane diterpenoids from Echinodorus macrophyllus . J. Nat. Prod. 2000 , 63 , 1576 – 1579 ; (h) James , G. D. ; Mills , S. D. ; Pattenden , G. Total synthesis of pukeleimide A, a 5-ylidenepyrrol-2(5H)-one from blue-green algae . J. Chem. Soc., Perkin Trans. 1 1993 , 2581 – 2584 .
  • Ma , D. ; Ma , J. ; Ding , W. ; Dai , L. An improved procedure to homochiral cyclic statines . Tetrahedron: Asymmetry 1996 , 7 , 2365 – 2370 .
  • (a) Casiraghi , G. ; Spanu , P. ; Rassu , G. ; Pinna , L. ; Ulgheri , F. Total syntheses of four isomers of cis-1,2-dihydroxypyrrolizidine . J. Org. Chem. 1994 , 59 , 2906 – 2909 ; (b) Klaver , W. J. ; Hiemstra , H. ; Speckamp , W. N. Synthesis and absolute configuration of the Aristotelia alkaloid peduncularine . J. Am. Chem. Soc. 1989 , 111 , 2588 – 2595 .
  • (a) Iwasawa , N. ; Maeyama , K. A highly efficient synthesis of (–)-PI-091 construction of the 4-alkoxy-2-butene-4-lactam skeleton from Fischer-type carbene complexes, alkynyllithiums, and tosyl isocyanate . J. Org. Chem. 1997 , 62 , 1918 – 1919 ; (b) Shiraki , R. ; Sumino , A. ; Tadano , K. ; Ogawa , S. Total synthesis of natural PI-091, a new platelet aggregation inhibitor of microbial origin . J. Org. Chem. 1996 , 61 , 2845 – 2852 ; (c) Pettit , G. R. ; Kamano , Y. ; Herald , C. L. ; Fujii , Y. ; Kizu , H. ; Boyd , M. R. ; Boettner , F. E. ; Doubek , D. L. ; Schmidt , J. M. ; Chapuis , J.-C. ; Michel , C. Isolation of dolastatins 10–15 from the marine mollusk Dolabella auricularia . Tetrahedron 1993 , 49 , 9151 – 9170 ; (d) Koehn , F. E. ; Longley , R. E. ; Reed , J. K. Microcolins A and B, new immunosuppressive peptides from the blue-green alga Lyngbya majuscula . J. Nat. Prod. 1992 , 55 , 613 – 619 .
  • (a) Pelletier , S. W. (Ed.); Alkaloids: Chemical and Biological Perspectives ; Wiley : New York , 1997 ; vol. 5 ; (b) Fuji , K. ; Yamada , T. ; Fujita , E. ; Murata , H. Lythraceous alkaloids, X: Alkaloids of Lagerstroemia subcostata and L. favriei: A contribution to the chemotaxonomy. Chem. Pharm. Bull. 1978, 26, 2515–2521; (c) Wiedhopf , R. M. ; Trumbull , E. R. ; Cole , T. R. Antitumor agents from Jatropha macrorhiza (euphorbiaceae) I: Isolation and characterization of jatropham. J. Pharm. Sci. 1973, 62, 1206–1207 .
  • Bosch , J. ; Roca , T. ; Catena , J.-L. ; Lorens , O. ; Perez , J.-J. ; Lagunas , C. ; Fernandez , A. G. ; Miquel , I. ; Fernandez-Serrat , A. ; Farrerons , C. Synthesis and biological evaluation of 1,3,4-triaryl-3-pyrrolin-2-ones, a new class of selective cyclooxygenase-2 inhibitors . Bioorg. Med. Chem. Lett. 2000 , 10 , 1745 – 1748 .
  • (a) Spaltenstein , A. ; Almond , M. R. ; Bock , W. J. ; Cleary , D. G. ; Furfine , E. S. ; Hazen , R. J. ; Kazmierski , W. M. ; Salituro , F. G. ; Tung , R. D. ; Wright , L. L. Novel inhibitors of HIV protease: Design, synthesis, and biological evaluation of picomolar inhibitors containing cyclic P1/P2 scaffolds. Bioorg. Med. Chem. Lett. 2000, 10, 1159–1162; (b) Smith , A. B. ; Hirschmann , R. ; Pasternak , A. ; Guzman , M. C. ; Yokoyama , A. ; Sprengeler , P. A. ; Darke , P. L. ; Emini , E. A. ; Schleif , W. A. Pyrrolinone-based HIV protease inhibitors: Design, synthesis, and antiviral activity: Evidence for improved transport. J. Am. Chem. Soc. 1995, 117, 11113–11123.
  • (a) Li , S.-H. ; Zhang , H.-J. ; Qiu , S.-X. ; Niu , X.-M. ; Santarsiero , B. D. ; Mesecar , A. D. ; Fong , H. H. S. ; Farnsworth , N. R. ; Sun , H. D. Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus . Tetrahedron Lett. 2002 , 43 , 5131 – 5134 ; (b) Carpes , M. J. S. ; Correia , C. R. D. Heck arylations of N-acyl-3-pyrroline and N-acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen, and analogues . Tetrahedron Lett. 2002 , 43 , 741 – 744 ; (c) Bhattia , S. H. ; Davies , G. M. ; Hitchcock , P. B. ; Loakes , D. ; Young , D. W. Synthesis of reactive γ-lactams related to penicillins and cephalosporins . J. Chem. Soc., Perkin Trans. 1 1999 , 2449 – 2454 ; (d) Davies , G. M. ; Hitchcock , P. B. ; Loakes , D. ; Young , D. W. Synthesis of reactive γ-lactams related to penicillins and cephalosporins . Tetrahedron Lett. 1996 , 37 , 5601 – 5604 ; (e) Fishwick , C. W. G. ; Foster , R. J. ; Carr , R. E. A short dipolar cycloaddition approach to γ-lactam alkaloids from Cynometra hankei . Tetrahedron Lett. 1996 , 37 , 3915 – 3918 ; (f) Mattern , R.-H. ; Gunasekera , S. ; McConnell , O. Synthetic studies of microcolin B . Tetrahedron 1996 , 52 , 425 – 434 ; (g) Koehn , F. E. ; McConnell , O. J. ; Longley , R. E. ; Sennett , S. H. ; Reed , J. K. Analogs of the marine immunosuppressant microcolin A: Preparation and biological activity . J. Med. Chem. 1994 , 37 , 3181 – 3186 ; (h) Zhang , H. ; Shigemori , H. ; Ishibashi , M. ; Kosaka , T. ; Pettit , G. R. ; Kamano , Y. ; Kobayashi , J. A short dipolar cycloaddition approach to γ-lactam alkaloids from cynometra hankei . Tetrahedron 1994 , 50 , 10201 – 10206 ; (i) Gamzu , E. R. ; Hoover , T. M. ; Gracon , S. I. ; Ninteman , M. V. Recent development in 2-pyrrolidinone-containing nootropics . Drug Dev. Res. 1989 , 18 , 177 – 189 ; (j) Baldwin , J. E. ; Freeman , R. T. ; Lowe , C. ; Schofield , C. J. ; Lee , E. A γ-lactam analogue of the penems possessing antibacterial activity . Tetrahedron 1989 , 45 , 4537 – 4550 ; (k) Ikuta , H. ; Shirota , H. ; Kobayashi , S. ; Yamagishi , Y. ; Yamada , K. ; Yamatsu , I. ; Katayama , K. Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones . J. Med. Chem. 1987 , 30 , 1995 – 1998 ; (l) Baldwin , J. E. ; Adlington , R. M. ; Jones , R. H. ; Schofield , C. J. ; Zaracostas , C. γ-Lactam analogues of carbapenicillanic acids . Tetrahedron 1986 , 42 , 4879 – 4888 ; (m) Boyd , D. B. ; Elzey , T. K. ; Hatfield , L. D. ; Kinnick , M. D. ; Morin , J. M. Jr. γ-Lactam analogues of the penems . Tetrahedron Lett. 1986 , 27 , 3453 – 3456 ; (n) Belaud , C. ; Roussakis , C. ; Letourneux , Y. ; El Alami , N. ; Villiéras , J. Synthesis of potential cytotoxic α-methylene γ-lactams . Synth. Commun. 1985 , 15 , 1233 – 1243 .
  • Pérard-Viret , J. ; Souquet , F. ; Manisse , M. L. ; Royer , J. An expeditious total synthesis of (±)-jamtine using condensation between imine and acid anhydride . Tetrahedron Lett. 2010 , 51 , 96 – 98 .
  • Reginato , G. ; Capperucci , A. ; Degl'Innocenti , A. ; Mordini , A. ; Pecchi , S. Stannylcupration of γ-heterosubstituted acetylenic esters: A new route to 4-stannylated five membered N- and O-heterocycles . Tetrahedron 1995 , 51 , 2129 – 2136 .
  • Tarnchompoo , B. ; Thebtaranonth , C. ; Thebtaranonth , Y. Pyrrolidine and α-methylene-α-lactam from the cyclization of α-(alkylaminoethyl)acrylate: Synthesis of aza-sarkomycins . Tetrahedron Lett. 1987 , 28 , 6675 – 6678 .
  • Besbes , R. ; Villiéras , M. ; Amri , H. Improved synthesis and reaction of dimethyl α–(bromomethyl) fumarate with primary amines . Indian J. Chem., Sect. B 1997 , 36B , 5 – 8 .
  • Torii , S. ; Inokuchi , T. ; Kubota , M. A practical access to methyl 3,3-dimethoxypropionates and N-protected β-aminoacrylates and β-aminoacrylonitrile by using electrochemical procedure. J. Org. Chem. 1985, 50, 4157–4160.
  • Galeazzi , R. ; Martelli , G. ; Natali , D. ; Orena , M. ; Rinaldi , S. Chiral 3-hydroxypyrrolidin-2-ones, Part 2: Stereodivergent synthesis of conformationally restricted analogues of β-homoserine . Tetrahedron: Asymmetry 2005 , 16 , 1779 – 1787 .
  • Deredas , D. ; Albrecht , L. ; Krawczyk , H. An efficient synthesis of β,γ,γ-trisubstituted-α-diethoxyphosphoryl-γ-lactams: A convenient approach to α-methylene-γ-lactams . Tetrahedron Lett. 2013 , 54 , 3088 – 3090 .
  • Gein , V. L. ; Kasimova , N. N. Three-component condensation of methyl acylpyruvates with aromatic aldehydes and ethylenediamine: Chemical properties of the products . Russ. J. Gen. Chem. 2005 , 75 , 254 – 260 .
  • Liu , R. ; Winston-McPherson , G. N. ; Yang , Z.-Y. ; Zhou , X. ; Song , W. ; Guzei , I. A. ; Xu , X. ; Tang , W. Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes . J. Am. Chem. Soc. 2013 , 135 , 8201 – 8204 .
  • (a) Villiéras , J. ; Rambaud , M. Wittig–Horner reaction in heterogeneous media, 1: An easy synthesis of ethyl α-hydroxymethylacrylate and ethyl α-halomethylacrylates using formaldehyde in water . Synthesis 1982 , 924 – 926 ; (b) Villiéras , J. ; Rambaud , M. ; Graff , M. Wittig–Horner reaction in heterogenous media, VII: A new strategy for the total syntheses of the royal jelly acid and the queen substance of honey bee . Synth. Commun. 1985 , 15 , 569 – 580 ; (c) Ben Ayed , T. ; Amri , H. A convenient synthesis of α-functional alkyl vinyl ketones . Synth. Commun. 1995 , 25 , 3813 – 3819 .
  • Loeffer , A. ; Pratt , R. D. ; Pucknat , J. ; Gelbart , G. ; Dreiding , A. S. Préparation des α-Méthylène Butyrolactones par Réaction de Reformatsky: Synthèse de l'Acide Protolichestérinique . Chimia 1969 , 23 , 413 – 416 .
  • Welch , S. C. ; Gruber , J. M. Synthesis of C-13-substituted retinoic acid analogs . J. Org. Chem. 1982 , 47 , 385 – 389 .
  • Nelson , R. P. ; McEuen , J. M. ; Lawton , R. G. α,α′-annulation of cyclic ketones: Synthesis of bicyclo [3.2.1]octane derivatives . J. Org. Chem. 1969 , 34 , 1225 – 1229 .
  • Dekkers , A. W. J. D. ; Speckman , W. N. ; Huisman , H. O. Addition of diethyl 2-bromomesaconate to N-tosylpiperidone enamine . Tetrahedron Lett. 1971 , 12 , 489 – 492 .
  • Labuschange , A. J. H. ; Malherbe , J. S. ; Meyer , C. J. ; Schneider , D. F. General synthesis of symmetrical and unsymmetrical organic sulphides under non-basic reaction conditions . J. Chem. Soc., Perkin Trans. 1 1978 , 955 – 961 , and references cited therein .
  • Garbers , C. F. ; Labuschagne , A. J. H. ; Meyer , C. J. ; Schneider , D. F. Stereospecific formation of a vinyl sulphide via a sulphonium ylide–salt coupling reaction . J. Chem. Soc., Perkin Trans. 1 1973 , 2016 – 2019 .
  • Sasaki , T. ; Kanematsu , K. ; Kakehi , A. ; Ito , G.-I. Molecular design by cycloaddition reactions, part IX: Further investigation of the cycloaddition reactions of pyridinium allylides [1-(1-pyridinio)prop-2-enides] to give indolizines . J. Chem. Soc., Perkin Trans. 1 1973 , 2089 – 2091 .
  • Zhujin , L. ; Guobin , R. Reaction of β-methyl-γ-oxo-α,β-unsaturated esters with NBS . Chin. J. Org. Chem. 1986 , 6 , 363 – 365 .
  • Ben Ayed , T. ; Amri , H. ; El Gaïed , M. M. Addition of bromine to β′-(functional alkyl) α,β-unsaturated esters stereoselective synthesis of β-haloderivatives . Tetrahedron 1991 , 47 , 9621 – 9628 .
  • Ben Gharbia , S. ; Besbes , R. ; Villiéras , M. ; Amri , H. Selected reaction of (Z)-dimethyl α-(bromomethyl)fumarate with secondary amines . Synth. Commun. 1996 , 26 , 1685 – 1692 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.