2-azido-1,3-dimethylimidazolinium chloride: An efficient diazo transfer reagent for 1,3-dicarbonyl compounds

Synlett

Volumn , Issue 18, 2009, Pages 2943-2944

  Kitamura, Mitsuru ^a   Tashiro, Norifumi ^a   Okauchi, Tatsuo ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Azides; Diazo compounds; Diazo transfer; Diazonium salt; Heterocycles

Indexed keywords

2 AZIDO 1,3 DIMETHYLIMIDAZOLINIUM CHLORIDE; CARBONYL DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIAZOTIZATION; HYDROLYSIS; ISOLATION PROCEDURE; SOLUBILITY; STEREOCHEMISTRY;

EID: 72049115785     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218269     Document Type: Article

References (30)

1. (a)For reviews, see:, Zhang Z, Wang J, Tetrahedron 2008 64 6577
2. (b)Doyle M P., Ye T, McKervey M A., Modern Catalytic Methods for Organic Synthesis with Diazo Compounds John Wiley & Sons New York 1998
3. (c)Ye T, McKervey M A., Chem. Rev. 1994 94 1091
4. (d)Padwa A, Austin D J., Angew. Chem. Int. Ed. Engl. 1994 33 1797
5. (e)Doyle M P., Chem. Rev. 1986 86 919
6. (a)For reviews on the synthesis of -diazo compounds by diazo transfer using tosyl azide, see:, Regitz M, Synthesis 1972 351
7. (b)Regitz M, Angew. Chem. Int. Ed. Engl. 1967 6 733
8. (a) For the use of alternative diazo transfer reagents and conditions, see: For imidazole-1-sulfonyl azide, see:, Goddard-Borger E D., Stick R V., Org. Lett. 2007 9 3797 For trifluorometanesulfonyl azide, see:
9. (b)Wurz R P., Lin W, Charette A B., Tetrahedron Lett. 2003 44 8845
10. (c) Cavender C J., Shiner V J. Jr., J. Org. Chem. 1972 37 3567
11. (d) For mesyl azide, see:, Taber D F., Ruckle R E. Jr., Hennessy M J., J. Org. Chem. 1986 51 4077
12. (e) For p-carboxybenzenesulfonyl azide, see:, Hendrickson J B., Wolf W A., J. Org. Chem. 1968 33 3610
13. (f) For 2-azido-3-ethylbenzothiazolium tetrafluoroborate, see:, Balli H, Löw R, Müller V, Rempfler H, Sezen-Gezgin A, Helv. Chim. Acta 1978 61 97
14. (g) For(azidochloromethylene)dimethylammonium chloride, see:, Kohel B, Viehe H G., Angew. Chem. Int. Ed. Engl. 1980 19 716
15. (h) For naphthalene-2-sulfonyl azide and p-(n-dodecyl)benzenesulfonyl azide, see:, Hazen G G., Weinstock L M., Connell R, Bollinger F W., Synth. Commun. 1981 11 947
16. (i) For 2,4,6-triisopropylphenyl-sulfonyl azide, see:, Lombardo L, Mander L N., Synthesis 1980 368
17. (j) For p -nitrophenyl azide, see:, Herbranson D E., Hawley M D., J. Electroanal. Chem. 1983 144 423
18. (k) For azidotris(diethylamino)-phosphonium bromide, see:, McGuiness M, Shechter H, Tetrahedron Lett. 1990 31 4987
19. (l) For polymer-bound sulfonyl azide, see:, Harned A M., Sherrill W M., Flynn D L., Hanson P R., Tetrahedron 2005 61 12093
20. (m) Green G M., Peet N P., Metz W A., J. Org. Chem. 2001 66 2509
21. (n) Roush W R., Feitler D, Rebek J, Tetrahedron Lett. 1974 15 1391
22. (o) For reaction in ionic liquid, see:, Ramachary D B., Narayana V V., Ramakumar K, Tetrahedron Lett. 2008 49 2704
23. (a) Hudlicky T, Govindan S V., Frazier J O., J. Org. Chem. 1985 50 4166
24. (b) Doyle M P., Dorow R L., Terpstra J W., Rodenhouse R A., J. Org. Chem. 1985 50 1663
25. (c) Ledon H, Synthesis 1974 347
26. Kitamura M, Chiba S, Narasaka K, Bull. Chem. Soc. Jpn. 2003 76 1063
27. The formation of salt 2 was confirmed by mass spectral analysis. The FAB(positive) mass spectrum of the mixture of the chloroimidazorium salt 3 and sodium azide showed a peak at m/z = 140, which corresponds to the calculated mass of [2 ? Cl?]+.
28. Typical procedure: [Caution: Although we have never had any trouble with azidoimidazolinium salt 2, it is potentially explosive.] To a solution of 2-chloro-1,3-dimethylimidazolinium chloride (3; 1.2 mmol) in acetonitrile (2 mL), sodium azide (1.2 mmol) was added at 0 ?C and the mixture was stirred for 30 min. 1,3-Dicarbonyl compound (1.0 mmol) and triethylamine (2.0 mmol) in THF (4 mL) was added to the mixture, which was stirred until the 1,3- dicarbonyl compound was consumed (reaction monitored by TLC). The reaction was quenched with water, and organic materials were extracted three times with CH2Cl2. The combined extracts were washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford the crude compound, which was almost pure. The crude materials were purified by flash column chromatography (silica gel: hexane?ethyl acetate) to give pure 2-diazo-1,3-dicarbonyl compound.
29. Ohira S, Synth. Commun. 1989 19 561
30. Müller S, Liepold B, Roth G J., Bestmann H J., Synlett 1996 521