Efficient method of synthesis of N,N′-disubstituted ureas/thioureas by a Zinc chloride catalyzed thermal reaction

Synthetic Communications

Volumn 39, Issue 16, 2009, Pages 2928-2934

  Pasha, M A ^a   Madhusudana Reddy, M B ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Disubstituted ureas thioureas; Solvent free reaction; Thermal condition; ZnCl2

Indexed keywords

ORGANIC SOLVENT; PHOSGENE; THIOUREA DERIVATIVE; UREA DERIVATIVE; ZINC CHLORIDE;

ARTICLE; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 67651092214     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802697467     Document Type: Article

References (16)

1. (a) Thavonekham, B. A practical synthesis of ureas from phenyl carbamates. Synthesis 1997, 10, 1189-1194;
2. (b) Armstrong, J. D.; Wolfe, C. N.; Keller, J. L.; Lynch, J.; Bhupathy, M.; Volante, R. P. A novel synthesis of disubstituted ureas using titanium(IV) isopropoxide and sodium borohydride. Tetrahedron Lett. 1997, 38, 1531-1532;
3. (c) Mikolajczyk, M.; Kielbasinski, P. Recent developments in the carbodiimide chemistry. Tetrahedron 1981, 37, 233-284;
4. (d) Paquette, L. (Ed.). Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: Chichester, UK, 1995; p. 4683.
5. Papesch, V.; Schroeder, E. F. Synthesis of 1-mono- and 1,3-di-substituted 6-aminouracils: Diuretic activity. J. Org. Chem. 1951, 16, 1879-1890.
6. Chen, J.; Ling, G.; Lu, S. Synthesis of new unsymmetric N,N′-dipyridylurea derivatives by selenium and selenium dioxide-catalyzed reductive carbonyla-tion of substituted nitropyridines. Tetrahedron 2003, 59, 8251-8256.
7. Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines. J. Org. Chem. 2004, 69, 4741-4750.
8. 2O-KI catalyzed, environmentally friendly synthesis of N,N′-disubstituted ureas in water under microwave irradiation. Synth. Commun. 2005, 35, 2325-2331.
9. (a) Pasha, M. A.; Manjula, K.; Jayashankara, V. P. Antimony-catalyzed simple, efficient, and solvent-free Friedel-Crafts acylation of aromatics under microwave irradiation. J. Saudi Chem. Soc. 2007, 11, 327-330;
10. (b) Pasha, M. A.; Jayashankara, V. P. Synthesis of α,α'- bis(arylmethylidene) cycloalkanones catalyzed by molecular iodine: An improved procedure for the Claisen-Schmidt condensation. Indian J. Chem. 2007, 46B, 1025-1027;
11. (c) Pasha, M. A.; Jayashankara, V. P.; Venugopala, K. N.; Rao, G. K. Zinc oxide (ZnO): An efficient catalyst for the synthesis of 4-arylidine-2-phenyl 5(4H)-oxazolones having antimicrobial activity J. Pharmacol. Toxicol. 2007, 2(3), 264-270;
12. (d) Pasha, M. A.; Jayashankara, V. P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a, j]xanthenes under solvent-free condition. Bioorg. Med. Chem. Lett. 2007, 17, 621-623;
13. (e) Pasha, M. A.; Jayashankara, V. P.p-Tolue-nesulfonic acid (p-TSA) catalyzed efficient synthesis of bis(indolyl) methanes under grindstone method. J. Pharmacol. Toxicol. 2006, 1(6), 573-578;
14. (f) Pasha, M. A.; Jayashankara, V. P. An expeditious synthesis of 1,5-benzodiazepine derivatives catalysed by zinc chloride. Heterocycles 2006, 5, 1017-1023;
15. 2: A simple and an efficient catalyst for esterification of phenols under solvent-free condition. Indian J. Chem. 2008, 47B, 597-600.
16. Pasha, M. A.; Jayashankara, V. P. Efficient synthesis of N,N′-disubstituted urea/thiourea catalyzed by iodine. Synth. Commun. 2006, 36, 1787-1793.