Download PDF
Synthesis 2003(16): 2525-2529  
DOI: 10.1055/s-2003-42404
PAPER
© Georg Thieme Verlag Stuttgart · New York

Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines

Radomir V. Smaliy*a, Aleksandra A. Chaikovskayaa, Aleksandr M. Pinchuka, Andrei A. Tolmachevb
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, 02094, Ukraine
b Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
Fax: +38(44)5732643; e-Mail: iochkiev@ukrpack.net;
Further Information

Publication History

Received 4 July 2003
Publication Date:
29 September 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

A study on the stepwise hydrolysis of hetarene- and cycloalkenecarboxamidophosphoryl dichlorides afforded the synthesis of hitherto unknown hetarene- and cycloalkene-carboxamidophosphoric acids as well as allowing the introduction of unsubstituted carbamoyl group in the molecules of pyrroles, indoles, indolizines, and some enamines.

Key words

carboxamides - isocyanatophosphoryl dichloride - carbonylamidophosphoric acids - indoles - pyrroles - indolizines - ena­mines

    References

  • 1 Barton D. Ollis WD. Comprehensive Organic Chemistry   Vol. 2:  Pergamon Press; Oxford: 1979.  Chap. 9.9.
    Search in Google Scholar
  • 2a Minisci F. Recupero F. Punta C. Gambarotti C. Antonietti F. Fontanab F. Pedullic GF. Chem. Commun.  2002,  21:  2496 
    CrossrefPubMedSearch in Google Scholar
  • 2b Scott MK. Baxter EW. Bennett DJ. Boyd RE. Blum PS. Codd EE. Kukla MJ. Malloy E. Maryanoff BE. Maryanoff CA. Ramussen CR. Raitz AB. Renzi MJ. Schwendler CF. Shank RP. Sherril RJ. Vaught JL. Villani FJ. Yim N. J. Med. Chem.  1995,  38:  4198 
    CrossrefPubMedSearch in Google Scholar
  • 2c Swain CJ. Baker R. Kneen C. Moseley J. Saunders J. Seward EM. Stevenson G. Beer M. Stanton J. Watling K. J. Med. Chem.  1991,  34:  140 
    CrossrefPubMedSearch in Google Scholar
  • 3a Rigo B. Fasseur D. Leduc C. Couturier D. Synth. Commun.  1990,  20:  1769 
    Search in Google Scholar
  • 3b Pindur U. Kim M.-H. Tetrahedron  1989,  45:  6427 
    Search in Google Scholar
  • 3c Gevorkyan KA. Papayan GL. Chshmarityan SG. Paronikyan RG. Akopyan NE. Pharm. Chem. J. (Engl.Transl.)  1988,  22:  1203 
    Search in Google Scholar
  • 3d Everett SA. Naylor MA. Stratford MRL. Patel KB. Ford E. Mortensen A. Ferguson AC. Vojnovic B. Wardman P. J. Chem. Soc., Perkin Trans 2  2001,  1989 
  • 3e Holland DO. Nayler JHL. J. Chem. Soc.  1955,  1504 
  • 4 Mehta G. Dhar D. Suri S. Synthesis  1978,  374 
    Thieme Connect
  • 5 Barnett GH. Anderson HJ. Loader CE. Can. J. Chem.  1980,  58:  409 
    Search in Google Scholar
  • 6 Smaliy RV. Chaikovskaya AA. Pinchuk AM. Tolmachev AA. Synthesis  2002,  2416 
    Thieme Connect
  • 7 Chaykovskaya AA. Smaliy RV. Tolmachev AA. Kudrya TN. Pinchuk AM. Heteroat. Chem.  1999,  10:  343 
    CrossrefSearch in Google Scholar
  • 8a Kirsanov AV. Makitra RG. Zh. Obshch. Khim.  1957,  27:  450 ; Chem. Abstr. 1957, 51, 15443
    Search in Google Scholar
  • 8b Derkach GI. Lepsa AM. Kirsanov AV. Zh. Obshch. Khim.  1962,  32:  2600 ; Chem. Abstr. 1963, 58, 8787
    Search in Google Scholar
  • 9a Kirsanov AV. Makitra RG. Zh. Obshch. Khim.  1956,  26:  905 ; Chem. Abstr. 1956, 50, 14600
    Search in Google Scholar
  • 9b Derkach GI. Dregval GF. Kirsanov AV. Zh. Obshch. Khim.  1962,  32:  150 ; Chem. Abstr. 1962, 57, 13668
    Search in Google Scholar