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

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

<A NAME="RP05903SS-1">1</A> Barton D. Ollis WD. Comprehensive Organic Chemistry Vol. 2: Pergamon Press; Oxford: 1979. Chap. 9.9.

<A NAME="RP05903SS-2A">2a</A> Minisci F. Recupero F. Punta C. Gambarotti C. Antonietti F. Fontanab F. Pedullic GF. Chem. Commun. 2002, 21: 2496

<A NAME="RP05903SS-2B">2b</A> 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

<A NAME="RP05903SS-2C">2c</A> 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

<A NAME="RP05903SS-3A">3a</A> Rigo B. Fasseur D. Leduc C. Couturier D. Synth. Commun. 1990, 20: 1769

<A NAME="RP05903SS-3B">3b</A> Pindur U. Kim M.-H. Tetrahedron 1989, 45: 6427

<A NAME="RP05903SS-3C">3c</A> Gevorkyan KA. Papayan GL. Chshmarityan SG. Paronikyan RG. Akopyan NE. Pharm. Chem. J. (Engl.Transl.) 1988, 22: 1203

<A NAME="RP05903SS-3D">3d</A> 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

<A NAME="RP05903SS-3E">3e</A> Holland DO. Nayler JHL. J. Chem. Soc. 1955, 1504

<A NAME="RP05903SS-4">4</A> Mehta G. Dhar D. Suri S. Synthesis 1978, 374

<A NAME="RP05903SS-5">5</A> Barnett GH. Anderson HJ. Loader CE. Can. J. Chem. 1980, 58: 409

<A NAME="RP05903SS-6">6</A> Smaliy RV. Chaikovskaya AA. Pinchuk AM. Tolmachev AA. Synthesis 2002, 2416

<A NAME="RP05903SS-7">7</A> Chaykovskaya AA. Smaliy RV. Tolmachev AA. Kudrya TN. Pinchuk AM. Heteroat. Chem. 1999, 10: 343

<A NAME="RP05903SS-8A">8a</A> Kirsanov AV. Makitra RG. Zh. Obshch. Khim. 1957, 27: 450 ; Chem. Abstr. 1957, 51, 15443

<A NAME="RP05903SS-8B">8b</A> Derkach GI. Lepsa AM. Kirsanov AV. Zh. Obshch. Khim. 1962, 32: 2600 ; Chem. Abstr. 1963, 58, 8787

<A NAME="RP05903SS-9A">9a</A> Kirsanov AV. Makitra RG. Zh. Obshch. Khim. 1956, 26: 905 ; Chem. Abstr. 1956, 50, 14600

<A NAME="RP05903SS-9B">9b</A> Derkach GI. Dregval GF. Kirsanov AV. Zh. Obshch. Khim. 1962, 32: 150 ; Chem. Abstr. 1962, 57, 13668