Control of site of lithiation of 3-(Aminomethyl)pyridine derivatives

Synthesis (Germany)

Volumn 45, Issue 24, 2013, Pages 3426-3434

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

^a CARDIFF UNIVERSITY   (United Kingdom)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

directed lithiation; N (pyridin 3 ylmethyl) pivalamide; N, N dimethyl N (pyridin 3 ylmethyl)urea; side chain lithiation; tert butyl N (pyridin 3 ylmethyl)carbamate

Indexed keywords

LITHIATION; LITHIUM DIISOPROPYLAMIDE; PYRIDINE DERIVATIVES; REFLUX CONDITIONS; SUBSTITUTION PRODUCTS; TERT -BUTYL N -(PYRIDIN-3-YLMETHYL)CARBAMATE; TETRA-HYDROFURAN; TRIFLUOROACETIC ANHYDRIDES;

CHAINS; DICHLOROMETHANE; LITHIUM; METABOLISM; UREA;

PYRIDINE;

1,1 DIPHENYL 2,3 DIHYDRO 1H PYRROLO[3,4-C]PYRIDINE; 1H PYRROLO[3,4 C]PYRIDINE; 3 (AMINOMETHYL)PYRIDINE DERIVATIVE; AMIDE; AMINE; CARBAMIC ACID DERIVATIVE; DICHLOROFLUOROMETHANE; LITHIUM DERIVATIVE; LITHIUM DIISOPROPYLAMIDE; N (PYRIDIN 3 YLMETHYL) DERIVATIVE; N (PYRIDIN 3 YLMETHYL)PIVALAMIDE; N (PYRIDIN 3 YLMETHYL)PIVALAMIDE TERT BUTYL N (PYRIDIN 3 YLMETHYL)CARBAMATE; N BUTYLLITHIUM; N,N DIMETHYL N' (PYRIDIN 3 YLMETHYL)UREA; NITROGEN; PYRIDINE DERIVATIVE; SUBSTITUTED N (PYRIDIN 3 YLMETHYL)PIVALAMIDE DERIVATIVE; SUBSTITUTED N (PYRIDINYLMETHYL)AMINE DERIVATIVE; TERT BUTYLLITHIUM; TETRAHYDROFURAN; TRIFLUOROACETIC ANHYDRIDE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COMPLEX FORMATION; LITHIATION; PROCESS CONTROL; REACTION TIME; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 84889887646     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338547     Document Type: Article

References (76)

1. Current address: Chemistry Department, College of Sciences and Humanities, Salman bin Abdulaziz University, P.O. Box 83, Al-Kharij 11942, Saudi Arabia.
2. Current address: Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt.
3. Clayden J. Organolithiums: Selectivity for Synthesis. Pergamon Oxford: 2002
4. Schlosser M. Organometallics in Synthesis. 2nd ed. Wiley Chichester: 2002; 1 352
5. El-Hiti G. A. Heterocycles: 2000; 53 1839
6. Mongin F., Quéguiner G. Tetrahedron: 2001; 57 4059
7. Turck A., Plé N., Mongin F., Quéguiner G. Tetrahedron: 2001; 57 4489
8. Anctil E. J.-G, Snieckus V. J. Organomet. Chem.: 2002; 653 150
9. Smith K., El-Hiti G. A. Curr. Org. Synth.: 2004; 1 253
10. Chinchilla R., Nájera C., Yus M. Chem. Rev.: 2004; 104 2667
11. Schlosser M. Angew. Chem. Int. Ed.: 2005; 44 376
12. Foubelo F., Yus M. Curr. Org. Chem.: 2005; 9 459
13. Rathman T. L., Bailey W. F. Org. Process Res. Dev.: 2009; 13 144
14. Florio S., Aggarwal V., Salomone A. Org. Lett.: 2004; 6 4191
15. Capriati V., Florio S., Luisi R. Chem. Rev.: 2008; 108 1918
16. Florio S., Capriati V., Salomone A. Top. Stereochem.: 2010; 26 135
17. Houlden C. E., Lloyd-Jones G. C., Booker-Milburn K. I. Org. Lett.: 2010; 12 3090
18. Volz N., Clayden J. Angew. Chem. Int. Ed.: 2011; 50 12148
19. El-Hiti G. A., Hegazy A. S., Alotaibi M. H., Ajarim M. D. ARKIVOC: 2012; (vii) 35
20. Clayden J., Turner H., Pickworth M., Adler T. Org. Lett.: 2005; 7 3147
21. Clayden J., Dufour J. Tetrahedron Lett.: 2006; 47 6945
22. Burgos P. O., Fernández I., Iglesias M. J., García-Granda S., Ortiz F. L. Org. Lett.: 2008; 10 537
23. Porcs-Makkay M., Komáromi A., Lukács G., Simig G. Tetrahedron: 2008; 64 1029
24. Michon C., Murai M., Nakatsu M., Uenishi J., Uemura M. Tetrahedron: 2009; 65 752
25. Tilly D., Fu J.-M, Zhao B.-P, Alessi M., Catanet A.-S, Snieckus V., Mortier J. Org. Lett.: 2010; 12 68
26. Slocum D. W., Wang S., White C. B., Whitley P. E. Tetrahedron: 2010; 66 4939
27. Cho I., Meimetis L., Belding L., Katz M. J., Dudding T., Britton R. Beilstein J. Org. Chem.: 2011; 7 1315
28. Schmid M., Waldner B., Schnürch M., Mihovilovic M. D., Stanetty P. Tetrahedron: 2011; 67 2895
29. Page A., Clayden J. Beilstein J. Org. Chem.: 2011; 7 1327
30. Coppi D. I., Salomone A., Perna F. M., Capriati V. Angew. Chem. Int. Ed.: 2012; 51 7532
31. Robert N., Bonneau A.-L, Hoarau C., Marsais F. Org. Lett.: 2006; 8 6071
32. Comoy C., Banaszak E., Fort Y. Tetrahedron: 2006; 62 6036
33. Luisi R., Capriati V., Florio S., Musio B. Org. Lett.: 2007; 9 1263
34. Clayden J., Hennecke U. Org. Lett.: 2008; 10 3567
35. McLaughlin M., Marcantonio K., Chen C., Davies I. W. J. Org. Chem.: 2008; 73 4309
36. Capriati V., Florio S., Luisi R., Mazzanti A., Musio B. J. Org. Chem.: 2008; 73 3197
37. Affortunato F., Florio S., Luisi R., Musio B. J. Org. Chem.: 2008; 73 9214
38. Musio B., Clarkson G. J., Shipman M., Florio S., Luisi R. Org. Lett.: 2009; 11 325
39. Capriati V., Florio S., Perna F. M., Salomone A. Chem. Eur. J.: 2010; 16 9778
40. Perna F. M., Salomone A., Dammacco M., Florio S., Capriati V. Chem. Eur. J.: 2011; 17 8216
41. Coppi D. I., Salomone A., Perna F. M., Capriati V. Chem. Commun.: 2011; 47 9918
42. Clayton J., Clayden J. Tetrahedron Lett.: 2011; 52 2436
43. Ibrahim N., Chevot F., Legraverend M. Tetrahedron Lett.: 2011; 52 305
44. Sheikh N. S., Leonori D., Barker G., Firth J. D., Campos K. R., Meijer A. J. H. M, O'Brien P., Coldham I. J. Am. Chem. Soc.: 2012; 134 5300
45. Smith K., El-Hiti G. A., Abdo M. A., Abdel-Megeed M. F. J. Chem. Soc., Perkin Trans. 1: 1995; 1029
46. Smith K., El-Hiti G. A., Abdel-Megeed M. F., Abdo M. A. J. Org. Chem.: 1996; 61 647
47. Smith K., El-Hiti G. A., Abdel-Megeed M. F., Abdo M. A. J. Org. Chem.: 1996; 61 656
48. Smith K., El-Hiti G. A., Pritchard G. J., Hamilton A. J. Chem. Soc., Perkin Trans. 1: 1999; 2299
49. Smith K., El-Hiti G. A., Shukla A. P. J. Chem. Soc., Perkin Trans. 1: 1999; 2305
50. Smith K., El-Hiti G. A., Hawes A. C. Synthesis: 2003; 2047
51. Smith K., El-Hiti G. A., Mahgoub S. A. Synthesis: 2003; 2345
52. El-Hiti G. A. Synthesis: 2003; 2799
53. Smith K., El-Hiti G. A., Abdel-Megeed M. F. Synthesis: 2004; 2121
54. El-Hiti G. A. Synthesis: 2004; 363
55. Smith K., El-Hiti G. A., Hegazy A. S. J. Sulfur Chem.: 2005; 26 121
56. Smith K., El-Hiti G. A., Hegazy A. S. Synthesis: 2005; 2951
57. Smith K., Barratt M. L. J. Org. Chem.: 2007; 72 1031
58. Padwa A., Bur S. Chem. Rev.: 2004; 104 2401
59. Kodama T., Tamura M., Oda T., Yamazaki Y., Nishikawa M., Takemura S., Doi T., Kyotani Y., Ohkuchi M. US 6605620B1: 2003
60. Katritzky A. R., Pozharskii A. F. Handbook of Heterocyclic Chemistry. 2nd ed. Pergamon Press New York: 2000
61. Craig P. N. Cumulative subject index and drug compendium In Comprehensive Medicinal Chemistry. Vol. 6 Hansch C., Sammes P. G., Taylor J. B. Pergamon Press Oxford: 1990
62. Güngör T., Marsais F., Quéguiner G. Synthesis: 1982; 499
63. Pomel V., Rovera J. C., Godard A., Marsais F., Quéguiner G. J. Heterocycl. Chem.: 1996; 33 1995
64. Godard A., Rocca P., Pomel V., Thomas-dit-Dumont L., Rovera J.-C, Thaburet J.-F, Marsais F., Quéguiner G. J. Organomet. Chem.: 1996; 517 25
65. Pollet P., Turck A., Plé N., Quéguiner G. J. Org. Chem.: 1999; 64 4512
66. Choppin S., Gros P., Fort Y. Eur. J. Org. Chem.: 2001; 603
67. Woltermann C. J., Schwindeman J. A. PharmaChem: 2002; 1 5; Chem. Abstr. 2004, 140, 94077
68. Turner J. A. J. Org. Chem.: 1983; 48 3401
69. Smith K., Anderson D., Matthews I. Sulfur Lett.: 1995; 18 79
70. Gros P., Choppin S., Mathieu J., Fort Y. J. Org. Chem.: 2002; 67 234
71. Lazaar J., Rebstock A.-S, Mongin F., Godard A., Trécourt F., Marsais F., Quéguiner G. Tetrahedron: 2002; 58 6723
72. Smith K., Lindsay C. M., Morris I. K., Matthews I., Pritchard G. J. Sulfur Lett.: 1994; 17 197
73. Watson S. E., Markovich A. Heterocycles: 1998; 48 2149
74. Numata A., Kondo Y., Sakamoto T. Synthesis: 1999; 306
75. Williard P. G., Li W., Kagan G., Hopson R. ARKIVOC: 2011; (v) 180
76. Bauer W., Winchester W. R., Schleyer P. von R. Organometallics: 1987; 6 2371