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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Three-Component Reaction of Triphenylphosphine, Dimethyl Acetylenedicarboxylate, and Aldehyde Benzoylhydrazones: An Efficient One-Pot Synthesis of Stable Phosphorus Ylides

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Pages 132-138 | Received 13 Dec 2008, Published online: 15 Feb 2011

REFERENCES

  • Corbridge , D. E. C. Phosphorus: An Outline of the Chemistry, Biochemistry, and Uses, , 5th ed.; Elsevier : Amsterdam , 1995 .
  • Engel , R. Synthesis of Carbon–Phosphorus Bonds ; CRC Press : Boca Raton , FL , 1988 .
  • Kolodiazhnyi , O. I. Methods of preparation of C-substituted phosphorus ylides and their application in organic synthesis . Russ. Chem. Rev. 1997 , 66 , 225 .
  • Bestmann , H. J. ; Zimmermann , R. Selected topics of the Wittig reaction in the synthesis of natural products . Top. Curr. Chem. 1983 , 109 , 85 .
  • Maryano , B. E. ; Reits , A. B. The Wittig olefination reaction and modification involving phosphoryl-stabilized carbanions: Stereochemistry, mechanism, and selected synthetic aspects . Chem. Rev. 1989 , 89 , 863 .
  • Pietrusiewiz , K. M. ; Zablocka , M. Preparation of scalemic p-chiral phosphines and their derivatives . Chem. Rev. 1994 , 94 , 1375 .
  • Aitken , R. A. ; Herion , H. ; Janosi , A. ; Karodia , N. ; Raut , S. ; Seth , V. S. ; Shannon , I. J. ; Smith , F. C. Flash vacuum pyrolysis of stabilised phosphorus ylides, part 5: Selective extrusion of PH3PO from b,c,b0-trioxo ylides to give diacylalkynes . J. Chem. Soc., Perkin Trans . 1 , 1994 , 2467 .
  • (a) Yavari , I. ; Maghsoodlou , M. T. ; Djahaniani , H. ; Hazeri , N. A facile synthesis of stable heterocyclic phosphorus ylides . J. Chem. Res., Synop. 1999 , 216 ; (b) Adib , M. ; Mostofi , M. ; Ghanbary , K. ; Bijanzadeh , H. Vinyltriphenylphosphonium salt-mediated efficient synthesis of iminophosphoraneds derived from 2-aminothiazoles . Synthesis 2005 , 10 , 1663 .
  • Yavari , I. ; Anary-Abbasinejad , M. Reaction between naphthols and dimethyl acetylenedicarboxylate in the presence of phosphites: Synthesis of stable oxa-2k5-phosphaphenanthrenes and benzochromene derivatives . Org. Biomol. Chem. 2003 , 3 , 560 .
  • Anary-Abbasinejad , M. ; Ascarrian , N. Stereoselective one-pot synthesis of functionalised phosphonates by three-component reaction between trimethylphosphite, dialkyl acetylenedicarboxylates, and aldehyde semicarbazones . J. Chem. Res. 2007 , 1 , 831 .
  • Anary-Abbasinejad , M. ; Tahan , S. Three-component reaction of triphenylphosphine, acetylenic esters, and aromatic amides: The synthesis of stable nitrogen-containing phosphorus ylides . Phosphorus, Sulfur Silicon Relat. Elem. 2007 , 2 , 315 .
  • Anary-Abbasinejad , M. ; Rostami , N. ; Parhami , A. ; Hassanabadi , A. Synthesis of functionalised phosphonates by three-component reaction between phosphites, dialkyl acetylenedicarboxylates and pyrrole, indole or benzotriazole . J. Chem. Res. 2007 , 257 .
  • Anary-Abbasinejad , M. ; Hassanabadi , A. ; Anaraki-Ardakani , H. One-pot synthesis of stable phosphite ylides by three component reaction between acetylenic esters, aldehyde semicarbazones and tributyl- or triethyl phosphite. J. Chem. Res. 2007, 455.
  • Anary-Abbasinejad , M. ; Hassanabadi , A. Stereoselective one-pot synthesis of functionalized phosphonates by three-component reaction between trialkyl (aryl) phosphites, dimethyl acetylenedicarboxylate, and indan-1,3-dione or N,N′-dimethyl barbituric acid . J. Chem. Res. 2007 , 475 .
  • Anary-Abbasinejad , M. ; Anaraki-Ardakani , H. ; Dehghan , A. ; Hassanabadi , A. ; Seyedmir , M. R. An effective one-pot synthesis of functionalized 3-pyrollin-2-ones by four-component reaction between triphenylphosphine, primary amines, dimethyl acetylenedicarboxylate, and ethyl chlorooxoacetate . J. Chem. Res. 2007 , 574 .
  • Anary-Abbasinejad , M. ; Anaraki-Ardakani , H. ; Ezadi , A. ; Hassanabadi, Three-component reaction between triphenylphosphine, acetylenic esters, and 4-hydroxycoumarin, 4-(phenylamino)coumarin, 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-1-methylquinolin-2(1H)-one . J. Chem. Res. 2007 , 605 .
  • Anary-Abbasinejad , M. ; Hassanabadi , A. ; Mazraeh-Seffid , M. Study of three-component reaction between trialkyl phosphites or triphenylphosphine, dimethyl acetylenedicarboxylate, and N-aryl-3-hydroxynaphthalene-2-carboxamide . J. Chem. Res. 2007 , 708 .
  • Anary-Abbasinejad , M. ; Anaraki-Ardakani , H. ; Hosseini-Mehdiabad , H. One-pot synthesis of stable phosphorus ylides by three-component reaction between dimethyl acetylenedicarboxylate, semicarbazones, and triphenylphosphine . Phosphorus, Sulfur and Silicon, Relat. Elem. 2008 , 1440 .
  • Anaraki-Ardakani , H. ; Sadeghian , S. ; Rastegari , F. ; Hassanabadi , A. ; Anary-Abbasinejad , M. Three-component reaction between triphenylphosphine, acetylenic esters, and arylsulfonyl hydrazides or aryl hydrazines: An efficient one-pot synthesis of stable β-nitrogen-substituted phosphorus ylides . Synth. Commun. 2008 , 38 , 1990 .
  • Tebby , J. C. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis ; J. C. Verkade and L. D. Quin (Eds.); VCH : Weinheim , 1987 ; chap. 1 , pp. 1 – 60 .
  • Vedejs , E. ; Snoble , K. A. J. Direct observation of oxaphosphetanes from typical Wittig reactions . J. Am. Chem. Soc. 1973 , 95 , 5778 .

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