Three-Component Reaction of Triphenylphosphine, Acetylenic Esters, and 6-Aminouracil or 6-Amino-N,N′-dimethyluracil

REFERENCES

• Wittig , G. From diyls to ylides to my idyll . Science 1980 , 210 , 600 .
   PubMed Web of Science ®Google Scholar
• Corbridge , D. E. C. Phosphorus: An Outline of the Chemistry, Biochemistry, and Uses, , 5th ed. ; Elsevier : Amsterdam , 1995 .
   Google Scholar
• Engel , R. Synthesis of Carbon–Phosphorus Bonds ; CRC Press : Boca Raton , FL , 1988 .
   Google Scholar
• Kolodiazhnyi , O. I. Methods of preparation of C-substituted phosphorus ylides and their application in organic synthesis . Russ. Chem. Rev. 1997 , 66 , 225 .
   Google Scholar
• Bestmann , H. J. ; Zimmermann , R. Selected topics of the Wittig reaction in the synthesis of natural products . Top. Curr. Chem. 1983 , 109 , 85 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Pietrusiewiz , K. M. ; Zablocka , M. Preparation of scalemic p-chiral phosphines and their derivatives . Chem. Rev. 1994 , 94 , 1375 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Yavari , I. ; Maghsoodlou , M. T. ; Djahaniani , H. ; Hazeri , N. A facile synthesis of stable heterocyclic phosphorus ylides . J. Chem. Res., Synop. 1999 , 216 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Anary-Abbasinejad , M. ; Mosslemin , M. H. ; Hassanabadi , A. ; Tabatabaee , M. Synthesis of alkyl (5-oxo-2-thioxo-[1,3,4] thiadiazinan-6-ylidene) acetates by the reaction between N-aminorhodanine, dialkyl acetylendicarboxylates, and triphenylphosphine . Synth. Commun. 2008 , 38 , 3700 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Mosslemin , M. H. ; Anary-Abbasinejad , M. ; Hassanabadi , A. ; Bagheri , M. A. Three-component reaction between triphenylphosphine, dialkyl acetylene dicarboxylate, and 4-amino-5-alkyl-2,4-dihydro-1,2,4-triazole-3-thiones: An efficient one-pot synthesis of stable phosphorus ylides . J. Sulfur Chem. 2010 , 31 , 135 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• Anary-Abbasinejad , M. ; Anaraki-Ardakani , H. ; Ezadi , A. ; Hassanabadi , A . 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 Silicon Relat. Elem. 2008 , 1440 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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.
   Google Scholar
• Vedejs , E. ; Snoble , K. A. J. Direct observation of oxaphosphetanes from typical Wittig reactions . J. Am. Chem. Soc. 1973 , 95 , 5778 .
   Web of Science ®Google Scholar