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

Radomir V. Smaliy; Aleksandra A. Chaikovskaya; Aleksandr M. Pinchuk; Andrei A. Tolmachev

doi:10.1055/s-2003-42404

PAPER

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

Radomir V. Smaliy*^a, Aleksandra A. Chaikovskaya^a, Aleksandr M. Pinchuk^a, Andrei A. Tolmachev^b
^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;

Abstract

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

Full Text

References

1 Barton D. Ollis WD. Comprehensive Organic Chemistry Vol. 2: Pergamon Press; Oxford: 1979. Chap. 9.9.

2a Minisci F. Recupero F. Punta C. Gambarotti C. Antonietti F. Fontanab F. Pedullic GF. Chem. Commun. 2002, 21: 2496

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

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

3a Rigo B. Fasseur D. Leduc C. Couturier D. Synth. Commun. 1990, 20: 1769

3b Pindur U. Kim M.-H. Tetrahedron 1989, 45: 6427

3c Gevorkyan KA. Papayan GL. Chshmarityan SG. Paronikyan RG. Akopyan NE. Pharm. Chem. J. (Engl.Transl.) 1988, 22: 1203

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

5 Barnett GH. Anderson HJ. Loader CE. Can. J. Chem. 1980, 58: 409

6 Smaliy RV. Chaikovskaya AA. Pinchuk AM. Tolmachev AA. Synthesis 2002, 2416

7 Chaykovskaya AA. Smaliy RV. Tolmachev AA. Kudrya TN. Pinchuk AM. Heteroat. Chem. 1999, 10: 343

8a Kirsanov AV. Makitra RG. Zh. Obshch. Khim. 1957, 27: 450 ; Chem. Abstr. 1957, 51, 15443

8b Derkach GI. Lepsa AM. Kirsanov AV. Zh. Obshch. Khim. 1962, 32: 2600 ; Chem. Abstr. 1963, 58, 8787

9a Kirsanov AV. Makitra RG. Zh. Obshch. Khim. 1956, 26: 905 ; Chem. Abstr. 1956, 50, 14600

9b Derkach GI. Dregval GF. Kirsanov AV. Zh. Obshch. Khim. 1962, 32: 150 ; Chem. Abstr. 1962, 57, 13668