- Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones
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A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.
- Kondoh, Azusa,Terada, Masahiro
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supporting information
p. 585 - 588
(2020/12/07)
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- Synthesis of fluorinated β-aminophosphonates and γ-lactams
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The functionalized polyfluorophosphorylated 1-azadienes I have been prepared by a Wittig reaction of ethyl glyoxalate and perfluorophosphorylated conjugated phosphoranes, obtained by reaction of phosphazenes and fluorinated acetylenic phosphonates. Subsequent reduction of both carbon-carbon and carbon-nitrogen double bonds of these 1-azadienes I affords the fluorine-containing β-aminophosphonates II, with the syn β-aminophosphonate being obtained as the major diastereoisomer. Base-mediated cyclocondensation of a diastereomeric mixture of aminophosphonates II leads exclusively to a new type of functionalized trans-γ-lactams III in a diastereoselective way. A computational study has also been used to explain the observed diastereoselectivity of these reactions.
- Alonso, Concepcion,Gonzalez, Maria,Fuertes, Maria,Rubiales, Gloria,Ezpeleta, Jose Maria,Palacios, Francisco
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p. 3858 - 3866
(2013/06/05)
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- Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: An efficient synthesis of aryliminophosphoranes under neutral and mild conditions
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An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields.
- Adib, Mehdi,Sheikhi, Ehsan,Deljoush, Azadeh
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experimental part
p. 4137 - 4140
(2011/06/24)
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- Copper(II) acetate/oxygen-mediated nucleophilic addition and intramolecular C-H activation/C-N or C-C bond formation: One-pot synthesis of benzimidazoles or quinazolines
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Diarylcarbodiimides or benzylphenylcarbodiimides are converted to 1,2-disubstituted benzimidazoles or 1,2-disustituted quinazolines via addition/intramolecular C-H bond activation/C-N or C-C bond forming reaction using copper(II) acetate/oxygen [Cu(OAc)2/O2] as the oxidant at 100°C in one-pot cascade procedure. Copyright
- He, Hua-Feng,Wang, Zhi-Jing,Bao, Weiliang
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supporting information; experimental part
p. 2905 - 2912
(2010/12/29)
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- Selective synthesis of 4-alkylidene-β-lactams and N,N′- diarylamidines from azides and aryloxyacetyl chlorides via a ketenimine-participating one-pot cascade process
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(Chemical Equation Presented) A one-pot cascade approach to 4-alkylidene-β-lactams and N,N-diarylamidines from aryl azides and aryloxyacetyl chlorides has been developed. The chemical outcome of the reaction can be controlled selectively by an appropriate choice of the stoichiometric ratio of different substrates and reagents. The products should find use in pharmaceutical discovery, especially in the development of new antimicrobial agents against multidrug-resistant pathogens.
- Yang, Yun-Yun,Shou, Wang-Ge,Hong, Deng,Wang, Yan-Guang
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p. 3574 - 3577
(2008/09/20)
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- The preparation of 1,2,3-trisubstituted guanidines
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An operationally straightforward and efficient benzotriazole-based method for the guanylation of diverse amines by use of the new reagent classes (bis-benzotriazol-1-yl-methylene)amines 13a-13f and benzotriazole-1- carboxamidines 17a-17i is described. The preparation is described for a variety of both acyclic and cyclic 1,2,3-trisubstituted guanidines in high yields.
- Katritzky, Alan R.,Khashab, Niveen M.,Bobrov, Sergey
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p. 1664 - 1675
(2007/10/03)
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- Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes
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Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dimethyl acetylenedicarboxylate and aromatic amines, such as aniline, 1-naphthylamine, p-toluidine, 4-bromoaniline, 4-nitroaniline, 4-acetylaniline, 2-aminopyridine, or 2-amino-5-bromopyridine. These stabilized phosphoranes undergo a smooth intramolecular reaction in boiling p-xylene or toluene to produce aryliminophosphoranes in excellent yields.
- Yavari, Issa,Adib, Mehdi,Hojabri, Leila
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p. 7213 - 7219
(2007/10/03)
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- Innovative synthesis of 4-carbaldehydepyrrolin-2-ones by zwitterionic rhodium catalyzed chemo- and regioselective tandem cyclohydrocarbonylation/CO insertion of α-imino alkynes
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The tandem cyclohydrocarbonylative/CO insertion of α-imino alkynes employs CO, H2, and catalytic quantities of zwitterionic rhodium complex (η6-C6H5 BPh3)-Rh+(1,5-COD) and triphenyl phosphite affording aldehyde substituted pyrrolinones in 67-82% yields. This unique transformation is readily applied to imino alkynes containing alkyl, alkoxyl, vinyl, and aryl substituents. The ability to prepare highly functionalized pyrrolinones makes this an attractive route to these important and versatile pharmaceuticals.
- Van den Hoven,Alper
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p. 10214 - 10220
(2007/10/03)
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- Complexes of N-aryltriphenylphosphinimines with mercury(II) halides
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The synthesis IR and 31P NMR spectra of the complexes of various N-aryltriphenylphosphinimines with some mercury dihalides as well as the corresponding phosphonium salts are reported It is shown by an X-ray crystal structure analysis of the complex of the unsubstituted phosphinimine with HgCl2 that in the solid state these complexes form dimers via two Hg...μ2 Cl...Hg bridges.
- Braun, Thomas P.,Gutsch, Paul A.,Zimmer, Hans
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p. 858 - 862
(2007/10/03)
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