Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 4
234
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of New 1,3‐bis(Heteroaryl)‐4,5‐imidazolidinediones Through Reaction of N,N′‐bis(Heteroaryl)methanediamines with Oxalyl Chloride

&
Pages 637-644 | Received 16 Mar 2006, Published online: 06 Mar 2007

References

  • Vogl , O. and Knight , A. C. 1968 . Polyoxamides, 1: Preparation and characterization of cyclic oxamides . Macromolecules , 1 : 311 – 315 .
  • Abeywickrama , C. and Baker , A. D. 2004 . Efficient synthesis of 1,4,5,12‐tetraazatriphenylene and derivatives . J. Org. Chem. , 69 : 7741 – 7744 .
  • Ulrich , H. and Sayigh , A. A. R. 1965 . The reaction of oxalyl chloride with substituted ureas and thioureas . J. Org. Chem. , 30 : 2781 – 2783 .
  • Deck , L. M. and Papadopoulos , E. P. 2003 . Reactions of isocyanates with methyl N‐(cyanothioformyl)anthranilate . J. Heterocycl. Chem. , 40 : 885 – 893 .
  • Hanafin , J. and Ben‐Ishai , D. 1976 . “ The reactions of bisamides with oxalyl chloride ” . In J. Heterocycl. Chem Vol. 13 , 889 – 890 .
  • Kunstler , R. , Erfurt , G. , Kochmann , W. , Riemer , J. , Pallas , M. and Issleib , K. Substituted 4,5‐imidazolidinediones . British Patent 1,255,767 . 1 Dec. 1971 . Chem. Abstr. 1972, 76, 34254v
  • Sharma , V. , Crankshaw , C. L. and Piwnica‐Worms , D. 1996 . Effects of multidrug resistance (MDRI) P‐glycoprotein essioxpren levels and coordination metal on the cytotoxic potency of multidentate (N4O2) (ethylenediamine)bis[propyl(R‐benzylimino)]metal(III) cations . J. Med. Chem. , 39 : 3483 – 3490 .
  • Sage , C. R. , Michelitsch , M. D. , Stout , T. J. , Biermann , D. , Nissen , R. , Finer‐Moore , J. and Stroud , R. M. 1998 . D221 in thymidylate synthase controls conformation change, and thereby opening of the imidazolidine . Biochemistry , 37 : 13893 – 13901 .
  • Gruber , W. and Dehler , J. 2,2‐Disubstituted 4,5‐imidazolidinediones . German Patent 2,018,433 . 28 Oct. 1971 . Chem. Abstr. 1972, 76, 34253u
  • Verardo , G. , Giumanini , A. G. , Gorassini , F. and Strazzolini , P. 1995 . Heterocycles from heterocycles: 1,3‐Dialkyl‐4,5‐imidazolidinediones from 1,3,5‐trialkylhexahydro‐1,3,5‐triazines and oxalyl chloride . Monatsh. Chem. , 126 : 103 – 105 .
  • Verardo , G. , Giumanini , A. G. , Gorassini , F. , Tolazzi , M. and Strazzohni , P. 1993 . Heterocycles from heterocycles: 1,3‐Diaryl‐4,5‐imidazolidinediones from 1,3,5‐triarylhexahydro‐1,3,5‐triazines and oxalyl chloride . Tetrahedron , 49 : 10609 – 10628 .
  • Marzona , M. and Carpignano , R. 1965 . Condensation of heterocyclic amines with formaldehyde. IV . Ann. Chim. , 55 : 1007 – 1013 .
  • Skowronska‐Serafinowa , B. 1955 . Some heterocyclic derivatives of methylenediamine . Roczniki Chem. , 29 : 932 – 933 .
  • Hunt , W. C. and Wagner , E. C. 1951 . The action of acids on alkylidene‐bis‐amines . J. Org. Chem. , 16 : 1792 – 1804 .
  • Kubicova , L. , Waisser , K. , Kunes , J. , Kralova , K. , Odlerova , Z. , Slosarek , M. , Janota , J. and Svoboda , Z. 2000 . Synthesis of N ,N′‐diarylalkanediamides and their antimycobacterial and antialgal activity . Molecules , 5 : 714 – 726 .
  • Kametani , T. , Kigasawa , K. and Hayasaka , T. 1968 . Syntheses of heterocyclic compounds, CCXXIII: Novel methylation, 6: N‐Methylation of primary amines and secondary amines with methyl salicylate and oxalate . Yakugaku Zasshi , 88 : 445 – 452 .
  • Cremlyn , R. I. 1974 . Synthesis and spectral data for some derivatives of N‐aryloxamic acid hydrazides . J. Chem. Eng. Data , 19 : 288 – 294 .
  • Perrin , D. D. , Armarego , W. L. F. and Perrin , D. R. 1980 . Purification of Laboratory Chemicals Exeter, , U.K. : A. Wheaton & Co. Ltd .

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.