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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 10
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Original Articles

Efficient Synthesis of 3-Methyl-2H-chromen-2-one: Classic Versus Microwave Conditions

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Pages 1514-1519 | Received 22 Dec 2009, Published online: 30 Mar 2011

REFERENCES

  • Graber , D. R. ; Grimes , M. W. ; Haug , A. Electron paramagnetic resonance studies of the triplet state of coumarin and related compounds . J. Chem. Phys. 1969 , 50 , 1623 – 1626 .
  • (a) Black , M. ; Cadogan , J. I. G. ; Cartwright , G. A. ; McNab , H. ; MacPherson , A. D. Carboxylic esters radical leaving groups: A new and efficient gas-phase synthesis of benzofurans. J. Chem. Soc., Chem. Commun. 1993, 959–960; (b) Kaye , P. T. ; Musa , M. A. Application of Baylis–Hillman methodology in the synthesis of coumarin derivatives. Synth. Commun. 2003, 33, 1755–1770.
  • Gopalan , B. ; Rajagopalan , K. ; Sunita , K. ; Balasubramanian , K. K. Studies in Claisen rearrangement: Novel thermal transformation of α-aryloxymethylacrylic acids and their derivatives . Tetrahedron 1985 , 41 , 3153 – 3159 .
  • Clinet , J. C. Conjugate additions on α-phenylthio-α,β-unsaturated oxazolines: Novel synthesis of 3,4-disubstituted coumarins . Tetrahedron Lett. 1988 , 29 , 5901 – 5904 .
  • Yoneda , E. ; Sugioka , T. ; Hirao , K. ; Zhang , S.-W. ; Takahashi , S. Rhodium-catalysed cyclic carbonylation of 2-alkynylphenols: Synthesis of benzofuranones and coumarins . J. Chem. Soc., Perkin Trans. 1 1998 , 477 – 484 .
  • Falsone , G. ; Spur , B. ; Wingen , P. H. Einfache Synthese von 3-Methyl-5,6-dihydro-2H-pyran-2-onen und 3-Methylcumarinen unter milden Bedingungen . Arch. Pharm. 1983 , 316 , 763 – 766 .
  • Perkin , W. H. On propionic coumarin and some of its derivatives . J. Chem. Soc. 1875 , 28 , 10 – 15 .
  • Mitra , A. K. ; Misra , S. K. ; Patra , A. New synthesis of 3-alkyl coumarins . Synth. Commun. 1980 , 10 , 915 – 919 .
  • Singer , L. A. ; Kong , N. P. Vinyl radicals: Stereoselectivity in hydrogen atom transfer to equilibrated isomeric vinyl radicals . J. Am. Chem. Soc. 1966 , 88 , 5213 – 5219 .
  • Dippy , J. F. J. ; Evans , R. M. The nature of the catalyst in the Perkin condensation . J. Org. Chem. 1950 , 15 , 451 – 456 .
  • Lácová , M. ; Chovancová , J. ; Konečný , V. Synthesis of 3-(aryl-X)coumarins and their pesticidal and antifungal activity . Chem. Papers 1986 , 40 , 121 – 126 .
  • Toräng , J. ; Vanderheiden , S. ; Nieger , M. ; Bräse , S. Synthesis of 3-alkylcoumarins from salicylaldehydes and α,β-unsaturated aldehydes utilizing nucleophilic carbenes: A new umpoled domino reaction . Eur. J. Org. Chem. 2007 , 943 – 952 .
  • Kisanga , P. ; Fei , X. ; Verkade , J. P(RNCH2CH2)3N: An efficient promoter for thesynthesis of 3-substituted coumarins . Synth. Commun. 2002 , 32 , 1135 – 1144 .
  • (a) Kulkami , V. S. ; Hosangadi , B. D. A facile synthesis of anhydro-dimers of o-hydroxybenzaldehydes . Synth. Commun. 1986 , 16 , 191 – 193 ; (b) Ragot , J. P. ; Prime , M. E. ; Archibald , S. J. ; Taylor , R. J. K. A novel route to preussomerins via 2-arylacetal anions . Org. Lett. 2000 , 2 , 1613 – 1616 ; (c) Adams , R. ; Fogler , M. F. ; Kreger , C. W. The structure of disalicylaldehyde . J. Am. Chem. Soc. 1922 , 44 , 1126 – 1133 ; (d) Voleva , V. B. ; Belostotskaya , I. S. ; Shishkin , O. V. ; Struchkov , Y. T. ; Ershov , V. V. Synthesis and structure of anhydrodimers of salicylaldehydes . Russ. Chem. Bull. 1995 , 44 , 1489 – 1491 .
  • Veverková , E. ; Pacherová , E. ; Toma , Š. Examination of the Perkin reaction under microwave irradiation . Chem. Papers 1999 , 53 , 257 – 259 .
  • Ogata , Y. ; Tsuchida , M. Kinetics and mechanism of the Perkin reaction . J. Org. Chem. 1959 , 24 , 78 – 83 .
  • Chandrasekhar , S. ; Karri , P. Revised mechanism and improved methodology for the Perkin condensation: Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride . Tetrahedron Lett. 2006 , 47 , 2249 – 2251 .
  • Xiang , D. ; Sun , K. Study of coumarin catalyzed by KNO3/γ-Al2O3 solid superbase . Yingyong Huagong 2005 , 34 , 288 – 289 .

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