Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 3
333
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Room-Temperature Synthesis and Antimicrobial Study of Novel 2-Aroylbenzofuran-3-ols from Substituted Methyl Salicylates and Phenacyl Bromides

, , , &
Pages 331-339 | Received 07 Mar 2013, Published online: 20 Nov 2013

REFERENCES

  • (a) Horton , D. A. ; Bourne , G. T. ; Smythe , M. L. Chem. Rev. 2003 , 103 , 893 – 930 ; (b) Palimkar , S. S. ; More , V. S. ; Srinivasan , K. V. Ultrasonics Sonochem. 2008 , 15 , 853 – 862 ; (c) Keay , B. A. ; Hopkins , J. M. ; Dibble , P. W. In Comprehensive Heterocyclic Chemistry III; A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor (Eds.); Elsevier: Oxford, 2008; (d) Gerard , B. ; Cencic , R. ; Pelletier , J. ; Porco Jr. , J. A. Angew. Chem. Int. Ed. 2007 , 46 , 7831 – 7834 ; (e) Pan , C. F. ; Ma , Z. ; Yu , J. ; Zhang , Z. ; Hui , A. ; Wang , Z. Synlett. 2005 , 12 , 1922 – 1926 .
  • (a) Marion , F. ; Williams , D. E. ; Patrick , B. O. ; Hollander , I. ; Mallon , R. ; Kim , S. C. ; Roll , D. M. ; Feldberg , L. ; Van Soest , R. ; Anderson , R. J. Org. Lett. 2006 , 8 , 321 – 324 ; (b) Yeung , K.-S. Furans and Benzofurans, Topics in Heterocyclic Chemistry; Springer-Verlag: Heidelberg , 2012 , pp. 47 – 76 ; (c) Mehta , G. ; Likhite , N. S. ; Ananda Kumar , C. S. Tetrahedron Lett. 2009 , 50 ( 37 ), 5260 – 5262 .
  • (a) Magometschnigg , D. ; Bonelli , J. ; Hitzenberger , G. ; Kaik , G. ; Korn , A. Int. J. Clin. Pharmacol. Biopharm. 1978 , 16 , 54 – 58 ; (b) Magometschnigg , D. ; Bonelli , J. ; Kaik , G. ; Rameis , H. Int. J. Clin. Pharmacol. Biopharm. 1979 , 17 , 334 – 340 .
  • (a) Fothergill , G. A. ; Osbond , J. M. ; Wickens , J. C. Arzneim.-Forsch. Drug Res. 1977 , 27 , 978 – 981 ; (b) Blaber , L. C. ; Burden , D. T. ; Eigeumann , R. ; Gerold , M. Cardiovasc. Pharmacol. 1984 , 6 , 165 – 175 .
  • Li , D. N. ; Pritchard , P. M. ; Hanlon , S. P. ; Burchell , B. ; Wolf , C. R. ; Friedberg , T. J. Pharmacol. Exp. Ther. 1999 , 289 , 661 – 667 .
  • (a) Marek , Z. ; Agnieszka , T.-K. ; Andrzej , P.-K. ; Aldona , C. Tetrahedron: Asymmetry 2003 , 14 , 1659 – 1664 , and the references cited therein .
  • Kim , S. ; Salim , A. A. ; Swanson , S. M. ; Kinghorn , A. D. Anticancer Agents Med. Chem. 2006 , 6 , 319 – 345 .
  • Whomsley , R. ; Fernandez , E. ; Nicholls , P. J. ; Smith , H. J. ; Lombardi , P. ; Pestellini , V. J. Steroid Biochem. Mol. Biol. 1993 , 44 , 675 – 676 .
  • Hayakawa , I. ; Shioya , R. ; Agatsuma , T. ; Furukawa , H. ; Naruto , S. ; Sugano , Y. Bioorg. Med. Chem. Lett. 2004 , 14 , 455 – 458 .
  • (a) Zhou , Z.-Z. ; Deng , Y.-H. ; Jiang , Z.-H. ; Chen , W.-H. Adv. Synth. Catal. 2010 , 352 , 1909 – 1913 ; (b) Patil , S. G. ; Bhadke , V. V. ; Bagul , R. R. J. Chem. Pharmaceut. Res. 2012 , 4 ( 5 ), 2832 – 2835 ; (c) Zhou , Z.-Z. ; Zou , M. ; Zhou , J. ; Zhou , C.-Q. ; Deng , Y.-H. ; Chen , M.-H. ; Gu , C.-P. ; Jiang , Z.-H. ; Chen , W.-H. ; Liu , S.-W. Chem. Pharm. Bull. 2011 , 59 ( 8 ), 1057 – 1061 ; (d) Earlier workers have referred to this reaction as Dieckmann condensation or Dieckmann cyclization. However, we prefer to call this Baker–Venkataraman-type reaction rather than Dieckmann cyclization, as this is cyclization of keto-ester to oxygen heterocycle akin to, but not identical to, the former reaction.
  • (a) Joshi , M. G. ; Wadodkar , K. N. Indian J. Chem. Sect. B 1981 , 20 ( 10 ), 930 – 931 ; (b) Gatta , F. ; Settimj , G. J. Heterocycl. Chem. 1984 , 21 ( 4 ), 937 – 943 ; (c) Mosher , W. A. ; Serridge , P. M. ; Lipp , D. W. J. Org. Chem. 1972 , 37 ( 15 ), 2402 – 2405 ; (d) Kevin , D. ; Paul , R. ; Robert , S. ; Allyson , T. ; David , W. ; Lee , A. U.S. Patent 6,297,238 B1 2001 ; Chem. Abstr. 2001 , 35 , 272953 .
  • (a) Pershadsingh , H. A. ; Levy , D. E. Patent WO Patent 2000000194 A1, 2000; Chem. Abstr. 2000, 132, 73666; (b) Kergoat , M. ; Leriche , C. ; Moinet , G. WO Patent WO2005054225 A1, 2005; Chem. Abstr. 2005, 143, 7588; (c) Bachmann , F. ; Eberle , M. ; Roy , S. ; Sadhukhan , S. K. ; Saha , G. ; Saxena , R. ; Srivastava , S. ; Strebel , A. WO Patent WO2005061476 A2, 2005; Chem. Abstr. 2005, 143, 115430.
  • (a) Bryant , R. J. Chem. Soc. 1965 , 5140 – 5141 ; (b) Bryant , R. ; Haslam , D. L. J. Chem. Soc. 1965 , 2361 – 2364 ; (c) Geissman , T. A. ; Armen , A. J. Am. Chem. Soc. 1955 , 77 ( 6 ), 1623 – 1627 .
  • (a) Mazumdar , A. K. D. ; Karmakar , P. K. ; Rangachari , K. ; Baneriee , K. P. ; Banerji , K. D. J. Indian Chem. Soc. 1990 , 67 , 911 – 913 ; (b) Rangachari , K. ; Mazumdar , A. K. D. ; Banerji , K. D. J. Indian Chem. Soc. 1980 , 57 , 1014 – 1016 .
  • (a) Prakash , O. ; Goyal , S. Synthesis , 1992 , 629 – 630 ; (b) Garg , C. P. ; Kapoor , R. P. Synth. Commun. 1992 , 22 , 2555 – 2561 ; (c) Prakash , O. ; Goyal , S. ; Pahuja , S. ; Singh , S. P. Synth. Commun. 1990 , 20 , 1409 – 1415 ; (d) Tokunaru , H. ; Masao , T. ; Yasuhiko , K. ; Shigeo , Y. Chem. Pharm. Bull. 1987 , 35 , 4465 – 4472 .
  • Botta , B. ; Delle , M. G. ; De Rosa , M. C. ; Scurria , R. ; Vitali , A. ; Vinciguerra , V. ; Menendez , P. Heterocycles 1996 , 43 , 1415 – 1421 .
  • (a) Anastas , P. T. ; Warner , J. C. Green Chemistry: Theory and Practice ; Oxford University Press : New York , 1998 ; (b) Sheldon , R. A. ; Arends , I. ; Hanefeld , U. Green Chemistry and Catalysis ; Wiley-VCH : Weinheim , 2007 ; pp. 295 – 324 .
  • (a) Perez , C. ; Paul , M. ; Chand , S. Acta Biologiae Med. Exp. 1990 , 15 , 113 – 115 ; (b) Nair , R. ; Kalariya , T. ; Chand , S. Turk. J. Biol. 2005 , 29 , 41 – 47 .

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.