Direct Access to N -Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure

Synthesis (Germany)

Volumn 47, Issue 13, 2015, Pages 1951-1959

  Dannenberg, Carl Albrecht ^a   Bizet, Vincent ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

imidation; oxidation; sulfide; sulfoximine; synthetic method

Indexed keywords

OXIDATION; SPEECH SYNTHESIS;

ALKYLATING REAGENTS; GRAM QUANTITIES; IMIDATION; ONE POT; SHORT PERIODS; SULFIDE; SULFOXIMINES; SYNTHETIC METHODS;

SULFUR COMPOUNDS;

ALIPHATIC AMINE; BROMINE DERIVATIVE; CHEMICAL COMPOUND; IMINE; N ALKYLSULFILIMINIUM BROMIDE; N ALKYLSULFOXIMINE; N BROMOALKYLAMINE; REAGENT; SULFIDE; SULFOXIMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; IMIDATION; ONE POT SYNTHESIS; OXIDATION;

EID: 84935011808     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1380536     Document Type: Article

References (50)

1. Reggelin M., Zur C. Synthesis: 2000; 1
2. Harmata M. Chemtracts: 2003; 16 660
3. Okamura H., Bolm C. Chem. Lett.: 2004; 33 482
4. Bolm C. In Asymmetric Synthesis with Chemical and Biological Methods. Enders D., Jaeger K.-E. Wiley-VCH Weinheim: 2007; 149
5. Gais H.-J. Heteroat. Chem.: 2007; 18 472
6. Bolm C. Latv. J. Chem.: 2012; 49
7. Bizet V., Kowalczyk R., Bolm C. Chem. Soc. Rev.: 2014; 43 2426
8. Shen X., Hu J. Eur. J. Org. Chem.: 2014; 4437
9. Wang J., Frings M., Bolm C. Angew. Chem. Int. Ed.: 2013; 52 8661; Angew. Chem. 2013, 125, 8823
10. Wang J., Frings M., Bolm C. Chem. Eur. J.: 2014; 20 966
11. Bizet V., Buglioni L., Bolm C. Angew. Chem. Int. Ed.: 2014; 53 5639; Angew. Chem. 2014, 126, 5745
12. Buglioni L., Bizet V., Bolm C.AAdv. Synth. Catal.: 2014; 356 2209
13. Miao J., Richards N. G. J, Ge H. Chem. Commun.: 2014; 50 9687; and references cited therein
14. For a recent overview about the use of sulfoximines in medicinal chemistry, see: Lücking U. Angew. Chem. Int. Ed.: 2013; 52 9399; Angew. Chem. 2013, 125, 9570
15. Lücking U., Jautelat R., Krueger M., Brumby T., Lienau P., Schaefer M., Briem H., Schulze J., Hillisch A., Reichel A., Wengner A. M., Siemeister G. ChemMedChem: 2013; 8 1067
16. Siemeister G., Lücking U., Wengner A. M., Lienau P., Steinke W., Schatz C., Mumberg D., Ziegelbauer K. Mol. Cancer Ther.: 2012; 11 2265
17. Krüger J., Gries J., Lovis K., Hassfeld J. Bayer Pharma AG, Patent WO 2012/038411 A1: 2012
18. Foote K. M., Nissink J. W. M, Turner P. AstraZeneca Patent WO 2011/154737 A1: 2011
19. Walker D. P., Zawistoski M. P., McGlynn M. A., Li J.-C, Kung D. W., Bonnette P. C., Baumann A., Buckbinder L., Houser J. A., Boer J., Mistry A., Han S., Xing L., Guzman-Perez A. Bioorg. Med. Chem. Lett.: 2009; 19 3253
20. Park S. J., Baars H., Mersmann S., Buschmann H., Baron J. M., Amann P. M., Czaja K., Hollert H., Bluhm K., Redelstein R., Bolm C. ChemMedChem: 2013; 8 217
21. Park S. J., Buschmann H., Bolm C. Bioorg. Med. Chem. Lett.: 2011; 21 4888
22. Zhu Y., Loso M. R., Watson G. B., Sparks T. C., Rogers R. B., Huang J. X., Gerwick B. C., Babcock J. M., Kelley D., Hegde V. B., Nugent B. M., Renga J. M., Denholm I., Gorman K., DeBoer G. J., Hasler J., Meade T., Thomas J. D. J. Agric. Food Chem.: 2011; 59 2950
23. Babcock J. M., Gerwick C. B., Huang J. X., Loso M. R., Nakamura G., Nolting S. P., Rogers R. B., Sparks T. C., Thomas J., Watson G. B., Zhu Y. Pest. Manag. Sci.: 2011; 67 328
24. Watson G. B., Loso M. R., Babcock J. M., Hasler J. M., Letherer T. J., Young C. D., Zhu Y., Casida J. E., Sparks T. C. Insect. Biochem. Mol. Biol.: 2011; 41 432
25. Sparks T. C., Loso M. R., Watson G. B., Babcock J. M., Kramer V. J., Zhu Y., Nugent B. M., Thomas J. D. In Modern Crop Protection Compounds. 2nd ed., Vol. 3; Kraemer W., Schirmer U., Jeschke P., Witschel M. Wiley-VCH Weinheim: 2012; 1226
26. L iberation, A bsorption, D istribution, M etabolism, E xcretion.
27. Goldberg F. W., Kettle J. G., Xiong J., Lin D. Tetrahedron: 2014; 70 6613
28. Bolm C., Hackenberger C. P. R, Simić O., Verrucci M., Müller D., Bienewald F. Synthesis: 2002; 879
29. Johnson C. R., Lavergne O. M. J. Org. Chem.: 1993; 58 1922
30. Raguse B., Ridley D. D. Aust. J. Chem.: 1986; 39 1655
31. Williams T. R., Cram D. J. J. Org. Chem.: 1973; 38 20
32. Hendriks C. M. M, Bohmann R. A., Bohlem M., Bolm C. AAdv.ASynth. Catal.: 2014; A356 1847
33. Williams T. R., Booms R. E., Cram D. J. J. Am. Chem. Soc.: 1971; 93 7338
34. Schmidbaur H., Kammel G. Chem. Ber.: 1971; 104 3234
35. Johnson C. R., Schroeck C. W., Shanklin J. R. J.AAm. Chem. Soc.: 1973; 95 7424
36. Johnson C. R., Corkins H. G. J. Org. Chem.: 1978; 43 4136
37. Johnson C. R., Rigau J. J., Haake M., McCants D. Jr, Keiser J. E., Gertsema A. Tetrahedron Lett.: 1968; 9 3719
38. Johnson C. R., Haake M., Schroeck C. W. J. Am. Chem. Soc.: 1970; 92 6594
39. Greenwald R. B., Evans D. H. Synthesis: 1977; 650
40. Brussaard Y., Olbrich F., Schaumann E. Inorg. Chem.: 2013; 52 13160
41. Tamura Y., Ikeda H., Morita I., Tsubouchi H., Ikeda M. Chem. Pharm. Bull.: 1982; 30 1221
42. Franek W., Claus P. K. Monatsh. Chem.: 1990; 121 539
43. Tamura Y., Minamikawa J., Sumoto K., Fujii S., Ikeda M. J. Org. Chem.: 1973; 38 1239
44. Mendiola J., Rincón J. A., Mateos C., Soriano J. F., de Frutos Ó, Niemeier J. K., Davis E. M. Org. Process Res. Dev.: 2009; 13 263
45. Bortolini O., Yang S. S., Cooks R. G. Org. Mass Spectrom.: 1993; 28 1313
46. Alternatively, the formation of the N -alkylsulfiliminium bromides 14 could be explained by reactions of the alkylamines with S -bromosulfonium salts being formed by initial bromine-to-sulfide additions. Here, however, this reaction path appears unlikely as all attempts to promote such process were unsuccessful leading to only complex product mixtures as revealed by NMR spectroscopy.
47. For an early work, see: Tsujihara K., Furukawa N., Oae K., Oae S. Bull. Chem. Soc. Jpn.: 1969; 42 2631
48. Initially, an equimolar mixture of MeNH2, Br2, und t -BuOK (1.4 equiv each) was applied for the imidation of sulfide 8a. Under these conditions, the conversion of 8a was only moderate (59%), and besides sulfiliminium salt 14a small amounts (2%) of sulfoxide 15a were detected.
49. For the thermal stability of sulfiliminium salts, see: Tamura Y., Matsushima H., Minamikawa J., Ikeda M., Sumoto K. Tetrahedron: 1975; 31 3035
50. Oae S., Masuda T., Tsujihara K., Furukawa N. Bull. Chem. Soc. Jpn.: 1972; 45 3586