Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 18
57
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

The Preparation of 2-Hydroxyethyl-2,3-dihydro-2h-1,4-benzoxazin-3(4h)-one Derivatives

&
Pages 3471-3478 | Received 06 Apr 1998, Published online: 22 Aug 2006

References

  • Cormican , M. G. and Jones , R. N. 1996 . Drugs , 51 ( Suppl. 1 ) : 6
  • Chu , D. T. W. , Plattner , J. J. and Katz , L. 1996 . J. Med. Chem. , 39 : 3853
  • Eliopoulos , G. M. , Wennersten , C. B. , Gold , H. S. and Moellering , R. C. Jr. 1996 . Antimicrob. Agents Chemother. , 40 : 1745
  • Brickner , S. J. , Hutchinson , D. K. , Barbachyn , M. R. , Manninen , P. R. , Ulanowicz , D. A. , Garmon , S. A. , Grega , K. C. , Hendges , S. K. , Toops , D. S. , Ford , C. W. and Zurenko , G. E. 1996 . J. Med. Chem. , 39 : 673
  • Tally , F. T. , Ellestad , G. A. and Testa , R. T. 1995 . J. Antimicrob. Chemother , 35 : 449
  • Sum , P.-E. , Lee , V. J. , Testa , R. T. , Hlavka , J. J. , Ellestad , G. A. , Bloom , J. D. , Gluzman , Y. and Tally , F. P. 1994 . J. Med. Chem. , 37 : 184
  • Onishi , H. R. , Pelak , B. A. , Gerckens , L. S. , Silver , L. L. , Kahan , F. M. , Chen , M.-H. , Patchett , A. A. , Galloway , S. M. , Hyland , S. A. , Anderson , M. S. and Raetz , C. R. H. 1996 . Science , 274 : 980
  • Russo , F. D. and Silhavy , T. J. 1993 . Trends Microbiol. , 1 : 306
  • Parkinson , J. S. and Kofoid , E. C. 1992 . Ann. Rev. Genetics , 26 : 71
  • Stock , J. B. , Ninfa , A. J. and Stock , A. M. 1989 . Microbiological Reviews , 53 : 450
  • Frechette , R. F. , Beach , M. J. , Bernstein , J. , Dow , T. , Foleno , B. , Johnson , C. E. , Loeloff , M. , Weidner-Wells , M. A. , Werblood , H. and Barrett , J. F. 1997 . Book of Abstracts, 214th ACS National Meeting . September 7–11 1997 , Las Vegas, NV. Washington, D. C. : Publisher: American Chemical Society .
  • Frechette , R. and Weidner-Wells , M. A. PCT Int. Appl. CODEN: PIXXD2. WO 9717333 A∗∗∗1 970515 165 .
  • Frechette , R. and Beach , M. PCT Int. Appl., CODEN: PIXXD2 WO 9728167 A∗∗∗1 970807 41 .
  • Shridhar , D. R. , Jogibhukta , M. and Krishnan , V. S. H. 1982 . Organic Preparations and Procedures Int. , 14 : 195
  • Masuoka , Y. , Asako , T. , Goto , G. and Noguchi , S. 1986 . Chem. Pharm. Bull. , 34 : 130
  • Kajino , M. , Shibouta , Y. , Nishikawa , K. and Meguro , K. 1991 . Chem. Pharm. Bull. , 39 : 2896
  • Shridhar , D. R. , Ram , B. , Rao , K. S. and Jain , M. L. 1985 . Indian J. Chem., Sect. B , 24B : 992
  • Combs , D. W. 1993 . Bioorg. Med. Chem. Lett. , 3 : 1663
  • Hogale , M. B. , Tarapure , V. T. , Shelar , A. R. and Jagdale , M. H. 1985 . J. Indian Chem. Soc. , 62 : 471
  • Shridhar , D. R. , Rao , K. S. , Singh , A. N. , Rastogi , K. , Jain , M. L. , Gandhi , S. S. , Krishnan , V. S. H. , Jogibhukta , M. , Lovekar , C. D. , Tripathi , H. N. and Sai , G. S. T. 1985 . Indian J. Chem., Sect. B , 24B : 1263
  • Hogale , M. B. , Nikam , B. P. and Dhore , N. P. 1985 . Orient. J. Chem. , 1 : 103
  • Sicker , D. , Hartenstein , H. , Hazard , R. and Tallec , A. 1994 . J. Heterocycl. Chem. , 31 : 809
  • Hydroxy substitution at the 2-position of the 1,4-benzoxazinone nucleus with 0, 1 and 3-carbon spacers have been reported:
  • Sicker , D. and Hartenstein , H. 1993 . Synthesis , : 771
  • Quiroz , A. and Niemeyer , H. M. 1991 . Heterocycles , 32 : 1681
  • Bartsch , H. and Schwarz , O. 1982 . J. Heterocycl. Chem. , 19 : 1189
  • Jacobi , P. A. , Craig , T. A. , Walker , D. G. , Arrick , B. A. and Frechette , R. F. 1984 . J. Am. Chem. Soc. , 106 : 5585
  • The nmr spectrum of the intermediate hydroxy acid was consistent with the structure. The structure was not rigorously proved, except by reconversion to the phenoxyfuranone derivative
  • In all cases, the products obtained after the crude workup were sufficiently pure to carry on as synthetic intermediates. Analytically pure material could be isolated after a single crystallization or trituration step. Yields shown reflect product obtained after purification at each step with, typically, only one crop collected following a crystallization or trituration procedure. Also, with the exception of the parent system ring (ie., 2a), product yields were the result of a single trial
  • Details of the structure activity relationships will be available in a manuscript which is in preparation

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.