Lithiation and substitution of N′ -(ω-phenylalkyl)-N,N- dimethylureas

Synthesis (Germany)

Volumn 44, Issue 13, 2012, Pages 2013-2022

  Smith, Keith ^a   El Hiti, Gamal A ^a,b   Alshammari, Mohammed B ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b Tanta University   (Egypt)

Author keywords

bromine lithium exchange; electrophile; N phenethyl N, N dimethylurea; side chain lithiation; synthesis

Indexed keywords

DIMETHYLUREA; ELECTROPHILES; LITHIATION; METHYL GROUP; METHYLLITHIUM; PHENYL RINGS; SIDE-CHAINS; TETRA-HYDROFURAN;

BROMINE; FUNCTIONAL GROUPS; LITHIUM; SYNTHESIS (CHEMICAL); UREA;

HYDROGEN BONDS;

BROMIDE; DIMETHYLUREA; ELECTROPHILE; LITHIUM; N' (2 BROMOPHENETHYL) N,N DIMETHYLUREA; N' (2 DEUTERIO 2 PHENYLETHYL) N,N DIMETHYLUREA; N' (2 HYDROXY 2,2 DIPHENYLETHYL) N' METHYL N (4 PHENYLBUTYL)UREA; N' (2 PHENYLBUTYL) N,N DIMETHYLUREA; N' (3 HYDROXY 2,3 DIPHENYLBUTYL) N,N DIMETHYLUREA; N' (3 HYDROXY 2,3 DIPHENYLPROPYL) N,N DIMETHYLUREA; N' (3 HYDROXY 2,3,3 TRIPHENYLPROPYL) N,N DIMETHYLUREA; N' (3 HYDROXY 3 METHYL 2 PHENYLBUTYL) N,N DIMETHYLUREA; N' (3 PHENYLPROPYL) N,N DIMETHYLUREA; N' (4 HYDROXY 3,4,4 TRIPHENYLBUTYL) N,N DIMETHYLUREA; N' (4 PHENYLBUTYL) N,N DIMETHYLUREA; N' (OMEGA PHENYLALKYL) N,N DIMETHYLUREA; N' 2 (2 DEUTERIOPHENYL)ETHYL N,N DIMETHYLUREA; N' 2 (3 BROMOPHENYL)ETHYL N,N DIMETHYLUREA; N' 2 [2 [HYDROXY(4 METHOXYPHENYL)METHYL]PHENYL]ETHYL N,N DIMETHYLUREA; N' 2 [2 [HYDROXY(PHENYL)METHYL]PHENYL]ETHYL N,N DIMETHYLUREA; N' 2 [3 (HYDROXYDIPHENYLMETHYL)PHENYL]ETHYL N,N DIMETHYLUREA; N' [2 (1 HYDROXYCYCLOHEXYL) 2 PHENYLETHYL] N,N DIMETHYLUREA; N' [2 (HYDROXYDIPHENYLMETHYL) 2 PHENYL]ETHYL N,N DIMETHYLUREA; N' ETHYL N' 2 (2 ETHYLPHENYL)ETHYL N,N DIMETHYLUREA; TERT BUTYLLITHIUM; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; LITHIATION; SYNTHESIS;

EID: 84862766249     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1291008     Document Type: Article

References (58)

1. Clayden J. Organolithiums: Selectivity for Synthesis. Pergamon Oxford: 2002
2. Schlosser M. Organometallics in Synthesis. 2nd ed. Wiley Chichester: 2002; 1 352
3. Gschwend HW, Hamdan A. J. Org. Chem.: 1975; 40 2008
4. Fitt JJ, Gschwend HW. J. Org. Chem.: 1976; 41 4029
5. Fuhrer W, Gschwend HW. J. Org. Chem.: 1979; 44 1133
6. Beak P, Snieckus V. Acc. Chem. Res.: 1982; 15 306
7. Nájera C, Sansano JM, Yus M. Tetrahedron: 2003; 59 9255
8. Whisler MC, MacNeil S, Snieckus V, Beak P. Angew. Chem. Int. Ed.: 2004; 43 2206
9. Chadwick ST, Ramirez A, Gupta L, Collum DB. J. Am. Chem. Soc.: 2007; 129 2259
10. Beak P, Zajdel WJ, Reitz DB. Chem. Rev.: 1984; 84 471
11. Snieckus V. Chem. Rev.: 1990; 90 879
12. El-Hiti GA. Heterocycles: 2000; 53 1839
13. Mongin F, Quéguiner G. Tetrahedron: 2001; 57 4059
14. Turck A, Plé N, Mongin F, Quéguiner G. Tetrahedron: 2001; 57 4489
15. Anctil EJ.-G, Snieckus V. J. Organomet. Chem.: 2002; 653 150
16. Smith K, El-Hiti GA. Curr. Org. Synth.: 2004; 1 253
17. Chinchilla R, Nájera C, Yus M. Chem. Rev.: 2004; 104 2667
18. Schlosser M. Angew. Chem. Int. Ed.: 2005; 44 376
19. Foubelo F, Yus M. Curr. Org. Chem.: 2005; 9 459
20. Rathman TL, Bailey WF. Org. Process Res. Dev.: 2009; 13 144
21. Florio S, Aggarwal V, Salomone A. Org. Lett.: 2004; 6 4191
22. Capriati V, Florio S, Luisi R. Chem. Rev.: 2008; 108 1918
23. Capriati V, Florio S, Salomone A. Top. Stereochem.: 2010; 26 135
24. Houlden CE, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett.: 2010; 12 3090
25. Clayden J, Turner H, Pickworth M, Adler T. Org. Lett.: 2005; 7 3147
26. Clayden J, Dufour J. Tetrahedron Lett.: 2006; 47 6945
27. Burgos PO, Fernández I, Iglesias MJ, García-Granda S, Ortiz FL. Org. Lett.: 2008; 10 537
28. Porcs-Makkay M, Komáromi A, Lukács G, Simig G. Tetrahedron: 2008; 64 1029
29. Michon C, Murai M, Nakatsu M, Uenishi J, Uemura M. Tetrahedron: 2009; 65 752
30. Tilly D, Fu J.-M, Zhao B.-P, Alessi M, Castanet A.-S, Snieckus V, Mortier J. Org. Lett.: 2010; 12 68
31. Slocum DW, Wang S, White CB, Whitley PE. Tetrahedron: 2010; 66 4939
32. Cho I, Meimetis L, Belding L, Katz MJ, Dudding T, Britton R. Beilstein J. Org. Chem.: 2011; 7 1315
33. Schmid M, Waldner B, Schnürch M, Mihovilovic MD, Stanetty P. Tetrahedron: 2011; 67 2895
34. Robert N, Bonneau A.-L, Hoarau C, Marsais F. Org. Lett.: 2006; 8 6071
35. Comoy C, Banaszak E, Fort Y. Tetrahedron: 2006; 62 6036
36. Luisi R, Capriati V, Florio S, Musio B. Org. Lett.: 2007; 9 1263
37. Clayden J, Hennecke U. Org. Lett.: 2008; 10 3567
38. McLaughlin M, Marcantonio K, Chen C, Davies IW. J. Org. Chem.: 2008; 73 4309
39. Capriati V, Florio S, Luisi R, Mazzanti A, Musio B. J. Org. Chem.: 2008; 73 3197
40. Affortunato F, Florio S, Luisi R, Musio B. J. Org. Chem.: 2008; 73 9214
41. Musio B, Clarkson GJ, Shipman M, Florio S, Luisi R. Org. Lett.: 2009; 11 325
42. Clayton J, Clayden J. Tetrahedron Lett.: 2011; 52 2436
43. Ibrahim N, Chevot F, Legraverend M. Tetrahedron Lett.: 2011; 52 305
44. Smith K, El-Hiti GA, Abdo MA, Abdel-Megeed MF. J. Chem. Soc., Perkin Trans. 1: 1995; 1029
45. Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA. J. Org. Chem.: 1996; 61 647
46. Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA. J. Org. Chem.: 1996; 61 656
47. Smith K, El-Hiti GA, Pritchard GJ, Hamilton A. J. Chem. Soc., Perkin Trans. 1: 1999; 2299
48. Smith K, El-Hiti GA, Shukla AP. J. Chem. Soc., Perkin Trans. 1: 1999; 2305
49. Smith K, El-Hiti GA, Hawes AC. Synthesis: 2003; 2047
50. Smith K, El-Hiti GA, Mahgoub SA. Synthesis: 2003; 2345
51. El-Hiti GA. Synthesis: 2003; 2799
52. Smith K, El-Hiti GA, Abdel-Megeed MF. Synthesis: 2004; 2121
53. El-Hiti GA. Synthesis: 2004; 363
54. Smith K, El-Hiti GA, Hegazy AS. J. Sulfur Chem.: 2005; 26 121
55. Smith K, El-Hiti GA, Hegazy AS. Synthesis: 2005; 2951
56. Smith K, Barratt ML. J. Org. Chem.: 2007; 72 1031
57. Wilson AA, Garcia A, Houle S, Sadovski O, Vasdev N. Chem.-Eur. J.: 2011; 17 259
58. Borgna P, Vicarini L, Calderara G. Farmaco: 1979; 33 510