Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 2
359
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Evaluation of Baylis–Hillman Routes to 3-(Aminomethyl)coumarin Derivatives

, , , , &
Pages 251-258 | Received 11 Apr 2013, Published online: 29 Oct 2013

REFERENCES

  • (a) Borges , F. ; Roleira , F. ; Milhazes , N. ; Santana , L. ; Uriarte , E. Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis, and biological activity . Curr. Med. Chem. 2005 , 12 , 887 – 916 ; (b) Lacy , A. ; O'Kennedy , R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer . Curr. Pharm. Des. 2004 , 10 , 3797 – 3811 ; (c) Leonetti , F. ; Favia , A. ; Rao , A. ; Aliano , R. ; Paluszcak , A. ; Hartmann , R. W. ; Carotti , A. Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors . J. Med. Chem. 2004 , 47 , 6792 – 6803 .
  • Thaisrivongs , S. ; Tomich , P. K. ; Watenpaugh , K. D. ; Chong , K. H. W. ; Howe , K. ; Yang , C. ; Strohbach , J. ; Tureer , S. ; McGrath , J. ; Bohanon , M. ; Lynn , J. ; Mulichak , A. ; Spinelli , P. ; Hinshaw , R. ; Pagano , P. ; Moon , J. ; Ruwart , M. ; Wilkinson , K. ; Rush , B. ; Zipp , G. ; Dalga , R. ; Schwende , F. ; Howard , G. P. G. ; Toth , L. ; Zhao , Z. ; Koeplinger , K. ; Kakuk , T. ; Cole , S. ; Zaya , R. ; Piper , R. ; Jeffrey , P. Structure-based design of HIV protease inhibitors: 4-hydroxycoumarins and 4-hydroxy-2-pyrones as non-peptidic inhibitors . J. Med. Chem. 1994 , 37 , 3200 .
  • Tummino , P. J. ; Ferguson , D. ; Hupe , D. Competitive inhibition of HIV-1 protease by warfarin derivatives . Biochem. Biophys. Res. Commun. 1994 , 201 , 290 ; (Chem. Abstr. 1994, 121, 73068.) .
  • Kaye , P. T. ; Robinson , R. S. DABCO-catalyzed reactions of salicylaldehydes with acrylate derivatives . Synth. Commun. 1996 , 26 , 2085 – 2097 .
  • Kaye , P. T. ; Musa , M. A. ; Nocanda , X. W. ; Robinson , R. S. Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis–Hillman pathway? Org. Biomol. Chem. 2003, 1, 1133–1138.
  • Kaye , P. T. ; Nocanda , X. W. A convenient general synthesis of 3-substituted 2H-chromene derivatives . J. Chem. Soc., Perkin Trans. 1 2002 , 1331 – 1332 .
  • Kaye , P. T. ; Musa , M. A. A convenient and improved Baylis–Hillman synthesis of 3-substituted 2H-1-benzopyran-2-ones . Synthesis 2002 , 2701 – 2706 .
  • Kaye , P. T. ; Musa , M. A. ; Nocanda , X. W. Efficient and chemoselective access to 3-(chloromethyl)coumarins via direct cyclization of unprotected Baylis–Hillman adducts . Synthesis 2003 , 531 – 534 .
  • Olomola , T. O. ; Klein , R. ; Lobb , K. A. ; Sayed , Y. ; Kaye , P. T. Towards the synthesis of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors . Tetrahedron Lett. 2010 , 51 , 6325 – 6328 .
  • Nagesam , M. ; Raju , M. S. ; Raju , K. M. Synthesis and antibacterial activity of 4,6-dimethyl-3-substituted-aminomethyl-coumarins . J. Indian Chem. Soc. 1987 , 64 , 418 – 419 ; Chem. Abstr. 1988, 221552.
  • Savel'ev , V. L. ; Artamonova , O. S. ; Troitskaya , V. S. ; Shavyrina , V. V. ; Afanas'eva , T. G. ; Zagorevskii , V. A. Synthesis and properties of 4-substituted 3-(aminomethyl)coumarins . Khim. Geterotsiklicheskikh Soedinenii 1982 , 896 – 899 ; Chem. Abstr. 1982, 562763.
  • Sokolov , A. V. ; Kirpichenok , M. A. ; Patalakha , N. S. ; Grandberg , I. I. Synthesis, luminescence, and acid–base properties of 3-(aminomethyl)-7-(dialkylamino)-coumarins . Khim. Geterotsiklicheskikh Soedinenii 1991 , 11 , 1494 – 501 ; Chem. Abstr. 1992, 492251.
  • Kovács , T. ; Ötvös , L. Simple synthesis of 5-vinyl- and 5-ethynyl-2′-deoxyuridine-5′-riphosphates . Tetrahedron Lett. 1988 , 29 , 4525 – 4528 .
  • Kaye , P. T. ; Musa , M. A. Regioselectivity of reactions of nitrogen and carbon nucleophiles with coumarin derivatives . Synth. Commun. 2004 , 34 , 3409 – 3417 .
  • Olomola , T. O. ; Klein , R. ; Kaye , P. T. Convenient synthesis of 3-methylcoumarins and coumarin-3-carbaldehydes . Synth. Commun. 2012 , 42 , 251 – 257 .
  • A C-13 signal at 124.3 ppm, hardly visible in the 1-D spectrum, was detected through its HMBC correlation with an aromatic methine proton .

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.